Organic electric element comprising organic compound and electronic device thereof

ABSTRACT

An organic electric element according to an embodiment of the present disclosure includes a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode. The organic material layer includes compounds represented by Formula 1 and Formula 2 of the present invention, thereby the driving voltage the organic electric element can be lowered, and the luminous efficiency and the life time of the organic electric element can be improved.

CROSS REFERENCE TO RELATED APPLICATIONS AND CLAIM OF PRIORITY

This application claims benefit under 35 U.S.C. 119, 120, 121, or 365(c), and is a National Stage entry from International Application No. PCT/KR2020/014520, filed Oct. 22, 2020, which claims priority to the benefit of Korean Patent Application No. 10-2019-0161865 filed in the Korean Intellectual Property Office on Dec. 6, 2019, the entire contents of which are incorporated herein by reference.

BACKGROUND 1. Technical Field

The present invention relates to organic electric element comprising organic compound and electronic device thereof.

2. Background Art

In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy of an organic material. An organic electric element utilizing the organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer interposed therebetween. In many cases, the organic material layer has a multi-layered structure having respectively different materials in order to improve efficiency and stability of an organic electric element, and for example, may comprise a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like.

Materials used as an organic material layer in an organic electric element may be classified into a light emitting material and a charge transport material, for example, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to its function. Further, the light emitting material may be divided into a high molecular weight type and a low molecular weight type according to its molecular weight, and may also be divided into a fluorescent material derived from excited singlet states of electron and a phosphorescent material derived from excited triplet states of electron according to its light emitting mechanism. Further, the light emitting material may be divided into blue, green, and red light emitting material and yellow and orange light emitting material required for better natural color reproduction according to its light emitting color.

Meanwhile, when only one material is used as a light emitting material, there occur problems of shift of a maximum luminescence wavelength to a longer wavelength due to intermolecular interactions and lowering of the efficiency of a corresponding element due to deterioration in color purity or a reduction in luminous efficiency. On account of this, a host/dopant system may be used as the light emitting material in order to enhance the color purity and increase the luminous efficiency through energy transfer. This is based on the principle that if a small amount of dopant having a smaller energy band gap than a host forming a light emitting layer is mixed in the light emitting layer, then excitons generated in the light emitting layer are transported to the dopant, thus emitting light with high efficiency. With regard to this, since the wavelength of the host is shifted to the wavelength band of the dopant, light having a desired wavelength can be obtained according the type of the dopant.

Currently, the power consumption is required more than more as size of display becomes larger and larger in the portable display market. Therefore, the power consumption is very important factor in the portable display with a limited power source of the battery, and efficiency and life span issues are also solved.

Efficiency, life span, driving voltage, and the like are correlated with each other. If efficiency is increased, then driving voltage is relatively lowered, and the crystallization of an organic material due to Joule heating generated during operation is reduced as driving voltage is lowered. As a result, life span tens to increase. However, efficiency cannot be maximized only by simply improving the organic material layer. This is because long life span and high efficiency can be simultaneously achieved when an optimal combination of energy levels and Ti values, inherent material properties (mobility, interfacial properties, etc.), and the like among the respective layers included in the organic material layer is given.

Therefore, there is a need to develop host material that has high thermal stability and can efficiently a charge balance in the light-emitting layer.

SUMMARY

An objection of the present invention is to provide organic electric element comprising the compound capable of lowering a driving voltage and improving luminous efficiency and lifetime of the element, and electronic device thereof.

The present invention provides organic electric element including compound represented by the following Formulas 1 and 2 in a light-emitting layer, and electronic device thereof.

By employing the mixture of compound represented by Formula 1 and compound represented by Formula 2 of the present invention as material of a light emitting layer, the driving voltage of the element can be lowered, and the luminous efficiency and lifespan of the element can be improved.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGS. 1 to 3 illustrate an example of organic electroluminescent element according to the present invention.

DETAILED DESCRIPTION

Unless otherwise stated, the term “aryl group” and “arylene group” as used herein has, but not limited to, 6 to 60 carbon atoms. The aryl group or arylene group in the present invention may comprise a monocyclic ring, ring assemblies, a fused polycyclic system, spiro compounds and the like.

As used herein, the term “fluorenyl group” refers to a substituted or unsubstituted fluorenyl group, “fluorenylene group” refers to a substituted or unsubstituted fluorenyl group. The fluorenyl group or fluorenylene group used in the present invention comprises a spiro compound formed by combining R and R′ with each other in the following structure, and also comprises compound formed by linking adjacent R″s to each other. “Substituted fluorenyl group”, “substituted fluorenylene group” means that at least one of R, R′, R″ in the following structure is a substituent other than hydrogen, and R″ may be 1 to 8 in the following formula.

The term “spiro compound” as used herein has a spiro union which means union having one atom as the only common member of two rings. The common atom is designated as ‘spiro atom’. The compounds are defined as ‘monospiro-’, ‘dispiro-’ or ‘trispiro-’ depending on the number of spiro atoms in one compound.

In addition, “fluorenyl group”, “fluorenylene group”, etc. as used herein are 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9′-spirofluorene, spiro[benzo[b]fluorene-11,9′-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene and the like.

The term “heterocyclic group” used in the specification comprises a non-aromatic ring as well as an aromatic ring like “heteroaryl group” or “heteroarylene group”. Unless otherwise stated, the term “heterocyclic group” means, but not limited to, a ring containing one or more heteroatoms and having 2 to 60 carbon atoms. Unless otherwise stated, the term “heteroatom” as used herein represents N, O, S, P or Si and the heterocyclic group means a monocyclic, ring assemblies, fused polycyclic system or spiro compound containing a heteroatom. In addition, heterocyclic group comprises compound comprising the heteroatom group such as SO₂, P═O and the like instead of carbon forming a ring like the following compound.

The term “aliphatic ring group” as used herein refers to a cyclic hydrocarbon except for aromatic hydrocarbons, and comprises a monocyclic ring, ring assemblies, a fused polycyclic system, spiro compounds, and the like, and unless otherwise stated, it means a ring of 3 to 60 carbon atoms, but not limited thereto. For example, a fused ring formed by benzene being an aromatic ring with cyclohexane being a non-aromatic ring corresponds to aliphatic ring group.

In this specification, a ‘group name’ corresponding to an aryl group, an arylene group, a heterocyclic group, and the like exemplified for each symbol and its substituent may be written in the name of functional group reflecting the valence, and may also be described as the name of a parent compound. For example, in the case of phenanthrene which is a kind of aryl group, it may be described by distinguishing valence such as ‘phenanthryl (group)’ when it is ‘monovalent group’, and as ‘phenanthrylene (group)’ when it is ‘divalent group’, and it may also be described as ‘phenanthrene’ being a parent compound name, regardless of its valence. Similarly, in the case of pyrimidine, it may be described as ‘pyrimidine’ regardless of its valence, and it may also be described as the name of corresponding functional group such as pyrimidinyl (group) when it is ‘monovalent group’, and as ‘pyrimidylene (group)’ when it is ‘divalent group’.

In addition, in the present specification, the numbers and alphabets indicating a position may be omitted when describing a compound name or a substituent name, For example, pyrido[4,3-d]pyrimidine, benzopuro[2,3-d]pyrimidine and 9,9-dimethyl-9H-fluorene can be described as pyridopyrimidine, benzofurropyrimidine and dimethylfluorene, respectively. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless expressly stated, the formula used in the present invention is applied in the same way as the definition of the substituent by the exponential definition of the following formula.

In the above formula, when a is an integer of zero, the substituent IV is absent, that is, hydrogen atoms are bonded to all the carbons constituting the benzene ring. Here, formulas or compounds can be described while omitting the representation of hydrogen bonded to carbon. In addition, one substituent IV is bonded to any one carbon of the carbons forming the benzene ring when “a” is an integer of 1, when “a” is an integer of 2 or 3, substituents R¹s may be bonded to the carbons of the benzene ring, for example, as followings and, when “a” is an integer of 4 to 6, substituents R¹s are bonded to the carbons of the benzene ring in a similar manner. Further, when “a” is an integer of 2 or more, R¹s may be the same as or different from each other.

In addition, unless otherwise described herein, when referring to a condensed/fused ring, the number in the ‘number-condensed ring’ indicates the number of condensed rings. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, and the like, may be represented by a 3-condensed ring.

In addition, unless otherwise described herein, in the case of expressing a ring in the form of a ‘number-membered’ such as a 5-membered ring or a 6-membered ring, the number in the ‘number-membered’ represents the number of atoms forming the ring. For example, thiophene or furan may correspond to a 5-membered ring, and benzene or pyridine may correspond to a 6-membered ring.

In addition, unless otherwise described herein, a ring formed by bonding adjacent groups to each other may be selected from the group consisting of a C₆-C₆₀ aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and a C₃-C₆₀ aliphatic ring. Unless otherwise stated, the term “between neighboring groups”, for an example, in the following Formulas, comprises not only “between R₁ and R₂”, “between R₂ and R₃”, “between R₃ and R₄”, “between R₅ and R₆”, but also “between R₇ and R₈” sharing one carbon, and may comprise “between substituents” attached to atoms (carbon or nitrogen) making up a ring such as “between R₁ and R₇”, “between R₁ and R₈”, or “between R₄ and R₅” and the like, which are not directly neighboring. That is, when there is substituent bonded to directly neighboring element such as carbon or nitrogen constituting a ring, the substituent may correspond to neighboring group, when no substituent is bonded to element constituting a ring at directly neighboring position, a substituent bonded to a next element constituting a ring may correspond to neighboring group, and substituents bonded to the same carbons constituting a ring may also be neighboring groups.

In the following Formulas, when the substituents bonded to the same carbon, such as R₇ and R₈, are linked to each other to form a ring, a compound containing a spiro-moiety may be formed.

In addition, in the present specification, the expression ‘neighboring (adjacent) groups may be linked to each other to form a ring’ is used in the same sense as ‘neighboring groups are linked selectively to each other to form a ring’, and a case where at least one pair of neighboring groups may be bonded to each other to form a ring.

In addition, unless otherwise specified in the present specification, an aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, and a ring formed by linking neighboring groups to each other may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a phosphine oxide group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group.

Hereinafter, referring to FIGS. 1 to 3 , a lamination structure of an organic electric element including compound of the present invention will be described.

In designation of reference numerals to components in respective drawings, it should be noted that the same elements will be designated by the same reference numerals although they are shown in different drawings. In addition, in describing the present invention, the detailed description of related and well-known configurations and functions will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the present invention, terms, such as first, second, A, B, (a), (b) or the like may be used. These terms are only for distinguishing the component from other components, and the essence, order, or order of the component is not limited by the term. It will be understood that the expression “one component is “connected,” “coupled” or “joined” to another component” comprises the case where a third component may be “connected,” “coupled,” and “joined” between the first and second components as well as the case where the first component may be directly connected, coupled or joined to the second component.

In addition, it will be understood that when an element such as a layer, film, region or substrate is referred to as being “on” or “over” another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

The FIGS. 1 to 3 are laminated structures showing an example of an organic electric element according to an embodiment of the present invention, respectively.

Referring to the FIG. 1 , an organic electric element 100 according to an embodiment of the present invention includes a first electrode 110 formed on a substrate (not shown), a second electrode 170, and an organic material layer formed between the first electrode 110 and the second electrode 170.

The first electrode 110 may be an anode (positive electrode), and the second electrode 170 may be a cathode (negative electrode). In the case of an inverted organic electric element, the first electrode may be a cathode, and the second electrode may be an anode.

The organic material layer may be comprised a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160. Specifically, a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160 are formed on the first electrode 110 in sequence.

Preferably, a layer for improving the luminous efficiency 180 may be formed one side of sides of the first electrode 110 or the second electrode 170, wherein the one side is not facing the organic material layer, as a result the luminous efficiency of an organic electric element can be improved.

For example, the light efficiency improving layer 180 may be formed on the second electrode 170, as a result, in the case of a top emission organic light emitting diode, the optical energy loss due to Surface Plasmon Polaritons (SPPs) at the second electrode 170 may be reduced and in the case of a bottom emission organic light emitting diode, the light efficiency improving layer 180 may serve as a buffer for the second electrode 170.

A buffer layer or an emission-auxiliary layer may be further formed between the hole transport layer 130 and the light emitting layer 140, which will be described with reference to FIG. 2 .

Referring to FIG. 2 , the organic electric element 200 according to another embodiment of the present invention may comprise a hole injection layer 120, a hole transport layer 130, a buffer layer 210, an emission-auxiliary layer 220, a light emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170 sequentially formed on a first electrode 110, and a light efficiency improving layer 180 may be formed on the second electrode 170.

Although not shown in FIG. 2 , an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.

In addition, according to another embodiment of the present invention, the organic material layer may be a form consisting of a plurality of stacks, wherein the stacks comprise a hole transport layer, a light emitting layer, and an electron transport layer, respectively. This will be described with reference to FIG. 3 .

Referring to FIG. 3 , two or more sets of stacks of organic material layers ST1 and ST2 may be formed between a first electrode 110 and a second electrode 170 of organic electric element 300 according to another embodiment of the present invention, wherein the organic material layers are consisted of multiple layers, respectively, and a charge generation layer CGL may be formed between the stacks of the organic material layer.

Specifically, organic electric element according to the embodiment of the present invention may comprise a first electrode 110, a first stack ST1, a charge generation layer CGL, a second stack ST2, and a second electrode 170 and a light efficiency improving layer 180.

The first stack ST1 is an organic layer formed on the first electrode 110, and the first stack ST1 may comprise a first hole injection layer 320, a first hole transport layer 330, a first light emitting layer 340 and a first electron transport layer 350 and the second stack ST2 may comprise a second hole injection layer 420, a second hole transport layer 430, a second light emitting layer 440 and a second electron transport layer 450. Like this, the first stack and the second stack may be organic material layers having the same or different stacked-structures.

The charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2. The charge generation layer CGL may comprise a first charge generation layer 360 and a second charge generation layer 361. The charge generating layer CGL is formed between a first light emitting layer 340 and a second light emitting layer 440 to increase the current efficiency generated in each of light emitting layers and to smoothly distribute charges.

The first light emitting layer 340 may comprise light emitting material comprising blue host doped with blue fluorescent dopant and the second light emitting layer 440 may comprise light emitting material comprising green host doped with greenish yellow dopant and red dopant together, but the material of the first light emitting layer 340 and the second light emitting layer 440 according to an embodiment of the present invention is not limited thereto.

In FIG. 3 , n may be an integer of 1 to 5 and the charge generation layer CGL and the third stack may be further stacked on the second stack ST2 when n is 2.

When a plurality of light emitting layers are formed in a multi-layer stack structure as shown in FIG. 3 , it is possible to manufacture organic electroluminescent element that emits not only white light but also various colors, wherein the white light is emitted by the mixing effect of light emitted from each of light emitting layers.

Even if the core is the same core, the band gap, the electrical characteristics, the interface characteristics and the like may be different depending on which substituent is bonded at which position. Therefore, it is necessary to study the selection of the core and a combination of the core and the sub-substituent bonded to the core. In particular, long life span and high efficiency can be simultaneously achieved when the optimal combination of energy levels and Ti values, inherent material properties (mobility, interfacial properties, etc.), and the like among the respective layers of an organic material layer is achieved.

Therefore, energy level and Ti value between the respective layers of the organic material layer, inherent material properties (mobility, interfacial properties, etc.) and the like can be optimized by using compounds represented by Formula 1 and the compound represented by Formula 2 as hosts for the light emitting layers 140, 340, and 440, and thus it is possible to simultaneously improve the lifetime and efficiency of the organic electric element.

Organic electric element according to an embodiment of the present invention may be manufactured using various deposition methods. Organic electric element according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method or CVD (chemical vapor deposition) method. For example, organic electric element may be manufactured by depositing a metal, conductive metal oxide or a mixture thereof on the substrate to form an anode 110, forming an organic material layer comprising a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160 on the anode, and then depositing material used as the cathode 170 on the organic material layer. Also, an emission-auxiliary layer 220 may be formed between a hole transport layer 130 and a light emitting layer 140, and an electron transport auxiliary layer (not shown) may be further formed between a light emitting layer 140 and an electron transport layer 150 and, as described above, a stack structure may be formed.

In addition, the organic material layer may be manufactured in such a manner that the fewer layers are formed using various polymer materials by a soluble process or solvent process, for example, spin coating, nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll, doctor blading, screen printing, or thermal transfer, instead of deposition. Since the organic material layer according to the present invention may be formed in various ways, the scope of protection of the present invention is not limited by a method forming the organic material layer.

Organic electric element according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a dual emission type depending on the material used.

In addition, organic electric element according to an embodiment of the present invention may be selected from the group consisting of an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, an element for monochromatic illumination and an element for quantum dot display.

Another embodiment of the present invention provides an electronic device including a display device which includes the above described organic electric element, and a control unit for controlling the display device. Here, the electronic device may be a wired/wireless communication terminal which is currently used or will be used in the future, and covers all kinds of electronic devices including a mobile communication terminal such as a cellular phone, a personal digital assistant (PDA), an electronic dictionary, a point-to-multipoint (PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, and various kinds of computers.

Hereinafter, an organic electric element according to one aspect of the present invention will be described.

An organic electric element according to one aspect of the present invention comprises a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a phosphorescent light emitting layer, and the host of the phosphorescent light emitting layer comprises a first compound represented by the following Formula 1 and a second compound represented by the following Formula 2.

First, Formula 1 will be described.

In Formula 1, each of symbols may be defined as follows.

Ar₁ to Ar₃, Ar₅ and Ar₆ are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and -L′-N(R_(a))(R_(b)).

L₁ to L₆ are each independently selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₃-C₆₀ aliphatic ring, and a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P.

n is 0 or 1, m is 1 or 2, and when m is 2, each of a plurality of L₂s, each of a plurality of L₃s, each of a plurality of Ar₂s, and each of a plurality of Ar₃s are the same as or different from each other.

L′ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₃-C₆₀ aliphatic ring, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a combination thereof.

R_(a) and R_(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₃-C₆₀ aliphatic ring, and a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P.

When at least one of Ar₁-Ar₃, Ar₅, Ar₆, R_(a) and R_(b) is an aryl group, the aryl group may be, for example, a C₆-C₃₀, a C₆-C₂₅, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group, specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, or the like.

When at least one of L₁-L₆ and L′ is an arylene group, the arylene group may be, for example, a C₆-C₃₀, a C₆-C₂₅, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ arylene group, specifically, phenyl, biphenyl, naphthyl, terphenyl, or the like.

When at least one of Ar₁-Ar₃, Ar₅, Ar₆, R_(a), R_(b), L₁-L₆ and L′ is a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₃₀, a C₂-C₂₆, a C₂-C₂₄, a C₂-C₂₃, a C₂-C₂₁, a C₂-C₂₀, a C₂-C₁₉, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇, a C₁₈, a C₁₉, a C₂₀, a C₂₁, a C₂₂, a C₂₃ or a C₂₄ heterocyclic group, specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, thiophene, pyrrole, silole, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, benzofuran, benzothiophene, benzoimidazole, benzothiazole, benzoxazole, benzosilole, dibenzofuran, dibenzothiophene, carbazole, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, phenanthroline, naphthobenzothiophene, naphthobenzofuran, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothienopyridine, benzofuropyridine, benzofuropyrimidine, phenanthrobenzothiophene, phenanthrobenzofuran, dinaphthothiophene, dinaphthofuran, phenanthroline, and the like.

When at least one of Ar₁-Ar₃, Ar₅, Ar₆, R_(a) and R_(b) is a fluorenyl group or at least one of L₁-L₆ is a fluorenylene group, the fluorenyl group or fluorenylene group may be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9′-spirobifluorene, spiro[benzo[b]fluorene-11,9′-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, and the like.

When at least one of Ar₁-Ar₃, Ar₅, Ar₆, R_(a) and R_(b) is an alkyl group, the alkyl group may be, for example, a C₁-C₂₀, a C₁-C₁₀, a C₁-C₄, a C₁, a C₂, a C₃ or a C₄ alkyl group, specifically, methyl, t-butyl, or the like.

When at least one of Ar₁-Ar₃, Ar₅, Ar₆, R_(a) and R_(b) is an alkenyl group, the alkenyl group may be, for example, a C₂-C₂₀, a C₂-C₁₀, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄ alkenyl group, specifically, methylene, ethylene, propylene, or the like.

For example, Formula 1 may be represented by one of the following Formula 1-A-1 to Formula 1-A-5.

In Formulas 1-A-1 to Formula 1-A-5, L₁ to L₃, Ar₂, Ar₃ and m are the same as defined for Formula 1.

L′ is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring.

Ar′ is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group.

R₁, R₂, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and neighboring groups may be linked to each other to form a ring.

Here, the term ‘neighboring groups’ may mean, for example, neighboring R₁s, neighboring R₂s, R′ and R″.

a and c are each an integer of 0-4, b is an integer of 0-3, and where each of these is an integer of 2 or more, each of R₁s and each of R₂s are the same as or different from each other.

When L′ is an arylene group, the arylene group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ arylene group.

When Ar′, R₁, R₂, R′ and R″ are an aryl group, the aryl group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group.

When L′, Ar′, R₁, R₂, R′ and R″ are further substituted with a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇, a C₁₈ heterocyclic group.

For example, Formula 1-A-1 may be represented by Formula 1-A-1a or 1-A-1b.

In Formulas 1-A-1a and 1-A-1b, each of symbols is the same as defined for Formula 1-A-1.

For example, Formula 11 may be represented by one of the following Formula 1-B-1 to Formula 1-B-4.

In Formulas 1-B-1 to 1-B-4, a and b are each an integer of 0-3, and where each of these is an integer of 2 or more, each of R₁s and each of R₂s are the same as or different from each other, and the rest of the symbols are the same as defined for Formulas 1-A-1 to 1-A-5.

For example, Formula 1 may be represented by one of the following Formula 1-C-1 to Formula 1-C-4.

In Formulas 1-C-1 to Formula 1-C-4, a is an integer of 0-4, b is an integer of 0-2, and where each of these is an integer of 2 or more, each of R₁s and each of R₂s are the same as or different from each other.

For example, Formula 1 may be represented by one of the following Formula 1-D-1 to Formula 1-D-3 or by one of the following Formula 1-E-1 to Formula 1-E-5.

In Formulas 1-D-1 to 1-D-3, and 1-E-1 to 1-E-5, x is an integer of 1-2, y is an integer of 0-1, z is an integer of 1-2, c is an integer of 0-5, d is an integer of 0-4, e is an integer of 0-3, and when c, d and e are each an integer of 2 or more, each of R₃s, each of R₄s, and each of R₅s are the same as or different from each other, and the rest of symbols are the same as defined in Formula 1.

In Formula 1 and each of the related formulas, each of symbols may be further substituted. For example, Ar₁-Ar₃, Ar₅, Ar₆, L₁-L₆, L′, R_(a), R_(b), R₁-R₅, R′, R″, Ar′ and the ring formed by linking neighboring groups to each other may be each substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group, and a C₅-C₂₀ arylalkenyl group.

When at least one of Ar₁-Ar₃, Ar₅, Ar₆, L₁-L₆, L′, R_(a), R_(b), R₁-R₅, R′, R″, Ar′ and the ring formed by linking neighboring groups to each other is further substituted with an aryl group, the aryl group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group.

When at least one of Ar₁-Ar₃, Ar₅, Ar₆, L₁-L₆, L′, R_(a), R_(b), R₁-R₅, R′, R″, Ar′ and the ring formed by linking neighboring groups to each other is further substituted with a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇ or a C₁₈ heterocyclic group.

When at least one of Ar₁-Ar₃, Ar₅, Ar₆, L₁-L₆, L′, R_(a), R_(b), R₁-R₅, R′, R″, Ar′ and the ring formed by linking neighboring groups to each other is further substituted with an alkyl group, the alkyl group may be, for example, a C₁-C₂₀, a C₁-C₁₀, a C₁-C₄, a C₁, a C₂, a C₃ or a C₄ alkyl group.

When at least one of Ar₁-Ar₃, Ar₅, Ar₆, L₁-L₆, L′, R_(a), R_(b), R₁-R₅, R′, R″, Ar′ and the ring formed by linking neighboring groups to each other is further substituted with a silane group substituted with an alkyl group, the alkyl group may be, for example, a C₁-C₁₀, a C₁-C₄, a C₁, a C₂, a C₃ or a C₄ alkyl group.

Next, the following Formula 2 will be described.

In Formula 2, each of symbols may be defined as follows.

In Formula 2, -(L1-Ar1) may be bonded to any of the four benzene rings constituting the backbone.

X¹ is N-L^(a)-Ar^(a), O or S.

IV to R⁴ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a C₁-C₃₀ alkyl group, a C₂-C₃₀ alkenyl group, a C₂-C₃₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)), and neighboring groups may be bonded to each other to form a ring. Here, the term ‘neighboring groups’ means, for example, neighboring R¹s, neighboring R²s, neighboring R³s, neighboring R⁴s, neighboring R¹ and L^(a), neighboring R¹ and Ar^(a), neighboring R² and L^(a), neighboring R¹ and Ar^(a) or the like.

p, q, r and s are an integer of 0 to 4, and where each of these is an integer of 2 or more, each of R¹s, each of R²s, each of R³s and each of R⁴s are the same as or different from each other,

Ar¹ is selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and -L′-N(R_(a))(R_(b)),

L¹ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₃-C₆₀ aliphatic ring, and a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P.

l is an integer of 0 to 4, and 1 is not 0 when X¹ is O or S. When 1 is an integer of 2 or more, each of the plurality of L¹s and each of the plurality of Ar¹s are the same as or different from each other.

L′ and L^(a) are each independently selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₃-C₆₀ aliphatic ring, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a combination thereof.

R_(a), R_(b) and Ar^(a) are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₃-C₆₀ aliphatic ring, and a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P.

When at least one of R¹-R⁴, Ar¹ is an aryl group, the aryl group may be, for example, a C₆-C₃₀, a C₆-C₂₅, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group, specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, or the like.

When L¹ is an arylene group, the arylene group may be, for example, a C₆-C₃₀, a C₆-C₂₅, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ arylene group, specifically, phenylene, biphenyl, naphthylene, terphenyl, or the like.

When at least one of R¹-R⁴, L¹ is a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₃₀, a C₂-C₂₆, a C₂-C₂₄, a C₂-C₂₃, a C₂-C₂₁, a C₂-C₂₀, a C₂-C₁₉, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a Cr, a C₁₈, a C₁₉, a C₂₀, a C₂₁, a C₂₂, a C₂₃ or a C₂₄ heterocyclic group, specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, carbazole, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, phenanthroline, naphthobenzothiophene, naphthobenzofuran, phenyl-carbazole, benzocarbazole, dinaphthothiophene, dinaphthofuran, phenanthroline, and the like.

When at least one of L′ and L^(a) is an arylene group, the arylene group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ arylene group.

When at least one of L′ and L^(a) is a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇ or a C₁₈ heterocyclic group,

When at least one of R_(a), R_(b) and Ar^(a) is an aryl group, the aryl group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group.

When at least one of R_(a), R_(b) and Ar^(a) is a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇ or a C₁₈ heterocyclic group.

When at least one of R¹-R⁴, Ar¹, R_(a), R_(b) and Ar^(a) is a fluorenyl group or L¹ is a fluorenylene group, the fluorenyl group or fluorenylene group may be, for example, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9′-spirobifluorene, spiro[benzo[b]fluorene-11,9′-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, and the like.

When at least one of R¹-R⁴ is an alkyl group, the alkyl group may be, for example, a C₁-C₂₀, a C₁-C₁₀, a C₁-C₄, a C₁, a C₂, a C₃ or a C₄ alkyl group, specifically, methyl, t-butyl, or the like.

For example, the ring formed by linking neighboring R¹s to each other, neighboring R²s to each other, neighboring R³s to each other, or neighboring R⁴s to each other may be a ring represented by one of the following Formulas F-1 to F-4.

In Formulas F-1 to F-4, the dotted line is the condensation site, and U is N-L_(a)-Ar_(a), C(R′)(R″), O or S.

R¹⁰ to R¹³, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and neighboring groups may be linked to each other to form a ring. Here, the term ‘neighboring groups’ may mean neighboring R¹⁰s, neighboring R¹¹s, neighboring R¹²s, neighboring R¹³s, R′ and R″, and the like.

a1 and a3 are each an integer of 0-4, a2 and a4 are each an integer of 0-6, and where each of these is an integer of 2 or more, each of R¹⁰s, each of R¹¹s, each of R¹²s and each of R¹³s are the same as or different from each other.

L_(a) is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring.

Ar_(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group.

When at least one of R¹⁰-R¹³, R′, R″ and Ar_(a) is an aryl group, the aryl group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group.

When L_(a) is an arylene group, the arylene group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ arylene group.

When at least one of R¹⁰-R¹³, R′, R″, Ar_(a) and L_(a) are a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇, a C₁₈ heterocyclic group.

For example, in Formula 2, R¹-R⁴ may be represented by one of Formula S-1 or S-2 below.

In Formulas S-1 and S-2, Y is N-L_(a)-Ar_(a), C(R′)(R″), O or S, and Q¹ to Q⁵ are each independently N or C(R′).

L_(A), L_(B) and L_(a) are each independently from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring.

Ar_(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group.

R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and adjacent groups may be linked to each other to form a ring, and R′ and R″ may be linked to each other to form a ring.

A ring formed by linking adjacent R's to each other or R′ and R″ groups to each other may be selected from the group consisting of a C₆-C₆₀ aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₆₀ aliphatic ring group. For example, in C(R′), when adjacent R's are linked to each other to form an aromatic ring formed, the aromatic ring may be a C₆-C₃₀, a C₆-C₂₅, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aromatic ring, for example, benzene, naphthalene, phenanthrene, or the like, and in C(R′)(R″), when a R′ and R″ are linked to each other to form a ring, a compound having a spirobifluorene skeleton may be formed.

When at least one of L_(A), L_(B) and L_(a) is an arylene group, the arylene group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ arylene group.

When at least one of Ar_(a), R′ and R″ is an aryl group, the aryl group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group.

When at least one of L_(A), L_(B), L_(a), Ar_(a), R′ and R″ is a heterocyclic group, the heterocyclic group may be, for example a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇ or a C₁₈ heterocyclic group.

For example, A ring and B ring may be each selected from the following structures.

In the above structures, * indicates a condensed position, Vs are each N or C(R′), at least one of Vs is N, W¹ and W² are each independently a single bond, N-L_(a)-Ar_(a), C(R′)(R″), O or S, and R′, R″, L_(a) and Ar_(a) are the same as defined in the above.

For example, Formula 2 may be represented by one of the following Formulas 2-A to 2-D.

In Formulas 2-A to 2-D, X is the same as X¹ of formula 2, and the remaining symbols are as defined for Formula 2.

R⁶ is selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and adjacent groups may be linked to each other to form a ring, f is an integer of 0-6, and when f is an integer of 2 or more, each of R⁶s is the same as or different from each other.

When R⁶ is an aryl group, the aryl group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group.

When R⁶ is a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a Cis, a C₁₆, a C₁₇, a Cis heterocyclic group.

For example, Formula 2 may be represented by one of the following Formulas 2-A-1 to 2-A-7.

In Formulas 2-A-1 to 2-A-7, x and y are each an integer of 0-4, x+y is an integer of 1 or more, and the same symbols as those of Formula 2 are the same as defined for Formula 2. That is, R¹-R⁴, L^(a), Ar^(a), L¹, p-s, l, etc. are the same as defined for Formula 2.

For example, Formula 2 may be represented by the following Formula 2-B-1.

In Formula 2-B-1, the same symbols as those of Formula 2 are the same as defined for Formula 2.

V is N-L_(a)-Ar_(a), C(R′)(R″), O or S.

R⁵, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and adjacent groups may be linked to each other to form a ring.

t is an integer of 0-7, and when t is an integer of 2 or more, each of R⁵ s is the same as or different from each other.

L_(a) is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring.

Ar_(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group.

When at least one of R⁵, R′, R″ and Ar_(a) is an aryl group, the aryl group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group.

When L_(a) is an arylene group, the arylene group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ arylene group.

When at least one of R⁵, R′, R″, Ar_(a) and L_(a) is a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇, a C₁₈ heterocyclic group.

Formula 2-B-1 may be represented by one of the following Formula 2-E to Formula 2-H.

In Formulas 2-E to 2-H, each of symbols is the same as defined for Formula 2-B-1, L_(b) is the same as L_(a), and Am is the same as Ar_(a).

For example, Formula 2 may be represented by one of the following Formulas 2-C-1 to 2-C-5.

In Formulas 2-C-1 to 2-C-5, the same symbols as those of Formula 2 are the same as defined for Formula 2, Y is N-L_(a)-Ar_(a), C(R′)(R″), O or S, and Vs are each independently Nor C(R′).

R_(e), R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and adjacent R's may be linked to each other to form a ring.

L_(a) is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring.

Ar_(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group.

When at least one of R_(e), R′, R″ and Ar_(a) is an aryl group, the aryl group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group.

When L_(a) is an arylene group, the arylene group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ arylene group.

When at least one of R_(e), R′, R″, Ar_(a) and L_(a) is a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇, a C₁₈ heterocyclic group.

In each of Formulas related to Formula 2, Ar¹, L¹, R¹-R⁴, L′, L^(a), Ar^(a), R_(a), R_(b) and the ring formed by linking neighboring groups to each other may be each further substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group, and a C₅-C₂₀ arylalkenyl group.

When at least one of Ar¹, L¹, R¹-R⁴, L′, L^(a), Ar^(a), R_(a), R_(b) and the ring formed by linking neighboring groups to each other is further substituted with an aryl group, the aryl group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group.

When at least one of Ar¹, L¹, R¹-R⁴, L′, L^(a), Ar^(a), R_(a), R_(b) and the ring formed by linking neighboring groups to each other is further substituted with a heterocyclic group, the heterocyclic group may be, for example a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₈, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇ or a C₁₈ heterocyclic group.

When at least one of Ar¹, L¹, R¹-R⁴, L′, L^(a), Ar^(a), R_(a), R_(b) and the ring formed by linking neighboring groups to each other is substituted with an alkyl group, the alkyl group may be, for example a C₁-C₂₀, a C₁-C₁₀, a C₁-C₄, a C₁, a C₂, a C₃ or a C₄ alkyl group, specifically, methyl, t-butyl, or the like.

For example, Formulas 1 and 2, L₁-L₆, L¹

may be independently one of Formulas b-1 to b-13.

In Formulas b-1 to b-13, Y is N-L_(a)-Ar_(a), C(R′)(R″), O or S, Z₁-Z₃ are independently N or C(R′), and at least one of Z₁-Z₃ is N.

R₁₁-R₁₃, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and adjacent groups may be linked to each other to form a ring.

L_(a) is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring.

Ar_(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group.

f is an integer of 0-4, h and i are each an integer of 0-3, j is an integer of 0-2, and where each of these is an integer of 2 or more, each of R₁₁s, each of R₁₂s, each of R₁₃s is the same as or different from each other.

When at least one of R₁₁-R₁₃, R′, R″ and Ar_(a) is an aryl group, the aryl group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ aryl group.

When L_(a) is an arylene group, the arylene group may be, for example, a C₆-C₁₈, a C₆-C₁₆, a C₆-C₁₄, a C₆-C₁₂, a C₆, a C₁₀, a C₁₂, a C₁₄, a C₁₆ or a C₁₈ arylene group.

When at least one of R₁₁-R₁₃, R′, R″, Ar_(a) and L_(a) is a heterocyclic group, the heterocyclic group may be, for example, a C₂-C₁₈, a C₂-C₁₆, a C₂-C₁₄, a C₂-C₁₃, a C₂-C₁₂, a C₂-C₁₁, a C₂-C₁₀, a C₂-C₉, a C₂-C₅, a C₂-C₇, a C₂-C₆, a C₂-C₅, a C₂-C₄, a C₂-C₃, a C₂, a C₃, a C₄, a C₅, a C₆, a C₇, a C₈, a C₉, a C₁₀, a C₁₁, a C₁₂, a C₁₃, a C₁₄, a C₁₅, a C₁₆, a C₁₇, a C₁₈ heterocyclic group.

Specifically, compound represented by formula 1 may be one of the following compounds, but there is no limitation thereto.

Specifically, the compound represented by formula 2 may be one of the following compounds, but there is no limitation thereto.

In an embodiment of the present invention, the host of the phosphorescent light emitting layer may be a mixture of the compound represented by Formula 1 and the compound represented by Formula 2 in a weight ratio of 2:8 to 8:2.

In another embodiment of the present invention, the organic material layer further comprises one or more hole transport band layers formed between the light-emitting layer and the anode, the hole transport band layers comprise at least one of a hole transport layer and an emission auxiliary layer and comprise the compound represented by Formula 1.

Hereinafter, examples for synthesizing the compounds represented by Formulas 1 and 2 will be described in detail with reference to examples, but the present invention is not limited to the following examples.

SYNTHESIS EXAMPLE [Synthesis Example of 1] Synthesis Example of Formula 1

The compound (final product 1, final product 1′) represented by Formula 1 according to the present invention may be prepared as shown in Reaction Schemes 1 and 2 below, but is not limited thereto. In Formula 1, the final product 1 may be synthesized by Reaction Scheme 1 when n is 0, and the final product 1′ may be synthesized by Reaction Scheme 2 when n is 1.

[Synthesis Example of 1-1] Synthesis Example of the Compound (Final Product 1′) Represented by Formula 1 1. Synthesis example of Sub 1-A

Sub 1-A of Reaction Scheme 1 may be the following structure, but is not limited thereto. Each of symbols is the same as defined in Formula 1-A-1, 1-A-2, 1-D-2, etc., y and z are 0 or 1, and at least one of y and z is 1.

Synthesis of Sub 1-A-a to Sub 1-A-c

The Sub 1-A-a to Sub 1-A-c may be synthesized by the reaction routes of the following Reaction Schemes 3 to 5, but are not limited thereto.

Synthesis Example of Sub 1-A-3

After 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (29.5 g, 80 mmol) was dissolved in THF (360 mL), 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd(PPh₃)₄ (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and water (180 mL) were added to the solution and the mixture was stirred under reflux. When the reaction was completed, the reaction product was extracted with ether and water. Then, an organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 22.9 g (72%) of the product.

Synthesis Example of Sub 1-A-5

After 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (73.92 g, 200.2 mmol) was dissolved in THF (880 mL), 1-bromo-2-iodobenzene (85.0 g, 300.3 mmol), Pd(PPh₃)₄ (11.6 g, 10 mmol), K₂CO₃ (83 g, 600.6 mmol) and water (440 mL) were added to the solution and the synthesis was carried out in the same manner as in the synthesis method of Sub 1-A-3 to obtain 55.8 g (yield: 70%) of the product.

Synthesis Example of Sub 1-A-61

After 4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-2-yl)-1,3,2-dioxaborolane (21 g, 61.01 mmol) was dissolved in THF (203 mL), 1,4-dibromonaphthalene (17.45 g, 61.01 mmol), Pd(PPh₃)₄ (2.82 g, 2.44 mmol), NaOH (7.32 g, 183.02 mmol) and water (102 mL) were added to the solution and the synthesis was carried out in the same manner as in the synthesis method of Sub 1-A-3 to obtain 22.9 g (75%) of the product.

Compounds belong to Sub 1-A are as follows, but are not limited thereto, and FD-MS values of the compounds are shown in Table 1 below.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-A-1 m/z = 321.02 (C₁₈H₁₂BrN = 322.21) Sub 1-A-2 m/z = 321.02 (C₁₈H₁₂BrN = 322.21) Sub 1-A-3 m/z = 397.05 (C₂₄H₁₆BrN = 398.30) Sub 1-A-4 m/z = 563.12 (C₃₇H₂₆BrN = 564.53) Sub 1-A-5 m/z = 397.05 (C₂₄H₁₆BrN = 398.30) Sub 1-A-6 m/z = 397.05 (C₂₄H₁₆BrN = 398.30) Sub 1-A-7 m/z = 473.08 (C₃₀H₂₀BrN = 474.40) Sub 1-A-8 m/z = 473.08 (C₃₀H₂₀BrN = 474.40) Sub 1-A-9 m/z = 473.08 (C₃₀H₂₀BrN = 474.40) Sub 1-A-10 m/z = 473.08 (C₃₀H₂₀BrN = 474.40) Sub 1-A-11 m/z = 473.08 (C₃₀H₂₀BrN = 474.40) Sub 1-A-12 m/z = 473.08 (C₃₀H₂₀BrN = 474.40) Sub 1-A-13 m/z = 497.08 (C₃₂H₂₀BrN = 498.42) Sub 1-A-14 m/z = 503.03 (C₃₀H₁₈BrNS = 504.45) Sub 1-A-15 m/z = 487.06 (C₃₀H₁₈BrNO = 488.38) Sub 1-A-16 m/z = 513.11 (C₃₃H₂₄BrN = 514.47) Sub 1-A-17 m/z = 473.08 (C₃₀H₂₀BrN = 474.40) Sub 1-A-18 m/z = 628.13 (C₃₉H₂₅BrN₄ = 629.56) Sub 1-A-19 m/z = 589.14 (C₃₉H₂₈BrN = 590.56) Sub 1-A-20 m/z = 627.13 (C₄₀H₂₆BrN₃ = 628.57) Sub 1-A-21 m/z = 473.08 (C₃₀H₂₀BrN = 474.40) Sub 1-A-27 m/z = 261.95 (C₁₂H₇BrS = 263.15) Sub 1-A-28 m/z = 337.98 (C₁₈H₁₁BrS = 339.25) Sub 1-A-29 m/z = 414.01 (C₂₄H₁₅BrS = 415.35) Sub 1-A-30 m/z = 454.04 (C₂₇H₁₉BrS = 455.41) Sub 1-A-31 m/z = 337.98 (C₁₈H₁₁BrS = 339.25) Sub 1-A-32 m/z = 337.98 (C₁₈H₁₁BrS = 339.25) Sub 1-A-33 m/z = 387.99 (C₂₂H₁₃BrS = 389.31) Sub 1-A-34 m/z = 464.02 (C₂₈H₁₇BrS = 465.41) Sub 1-A-35 m/z = 438.01 (C₂₆H₁₅BrS = 439.37) Sub 1-A-36 m/z = 387.99 (C₂₂H₁₃BrS = 389.31) Sub 1-A-37 m/z = 311.96 (C₁₆H₉BrS = 313.21) Sub 1-A-38 m/z = 414.01 (C₂₄H₁₈BrS = 415.35) Sub 1-A-39 m/z = 569.06 (C₃₃H₂₀BrN₃S = 570.51) Sub 1-A-40 m/z = 579.07 (C₃₆H₂₂BrNS = 580.54) Sub 1-A-41 m/z = 387.99 (C₂₂H₁₃BrS = 389.31) Sub 1-A-42 m/z = 311.96 (C₁₆H₉BrS = 313.21) Sub 1-A-43 m/z = 378.01 (C₂₁H₁₅BrS = 379.32) Sub 1-A-44 m/z = 438.01 (C₂₆H₁₅BrS = 439.37) Sub 1-A-45 m/z = 398.03 (C₂₄H₁₅BrO = 399.29) Sub 1-A-46 m/z = 438.06 (C₂₇H₁₉BrO = 439.35) Sub 1-A-47 m/z = 245.97 (C₁₂H₇BrO = 247.09) Sub 1-A-48 m/z = 322 (C₁₈H₁₁BrO = 323.19) Sub 1-A-49 m/z = 372.01 (C₂₂H₁₃BrO = 373.25) Sub 1-A-50 m/z = 422.03 (C₂₆H₁₅BrO = 423.31) Sub 1-A-51 m/z = 295.98 (C₁₆H₉BrO = 297.15) Sub 1-A-52 m/z = 322 (C₁₈H₁₁BrO = 323.19) Sub 1-A-53 m/z = 322 (C₁₈H₁₁BrO = 323.19) Sub 1-A-63 m/z = 228.07 (C₁₅H₁₃Cl = 228.72) Sub 1-A-64 m/z = 228.07 (C₁₅H₁₃Cl = 228.72) Sub 1-A-65 m/z = 228.07 (C₁₅H₁₃Cl = 228.72) Sub 1-A-66 m/z = 380.13 (C₂₇H₂₁Cl = 380.92) Sub 1-A-67 m/z = 348.05 (C₂₁H₁₇Br = 349.27) Sub 1-A-68 m/z = 424.08 (C₂₇H₂₁Br = 425.37) Sub 1-A-69 m/z = 500.11 (C₃₃H₂₅Br = 501.47) Sub 1-A-70 m/z = 348.05 (C₂₁H₁₇Br = 349.27) Sub 1-A-71 m/z = 500.11 (C₃₃H₂₅Br = 501.47) Sub 1-A-72 m/z = 464.11 (C₃₀H₂₅Br = 465.43) Sub 1-A-73 m/z = 448.08 (C₂₉H₂₁Br = 449.39) Sub 1-A-74 m/z = 352.10 (C₂₅H₁₇Cl = 352.86) Sub 1-A-75 m/z = 462.09 (C₃₁H₂₀Cl₂ = 463.40) Sub 1-A-76 m/z = 352.10 (C₂₅H₁₇Cl = 352.86) Sub 1-A-77 m/z = 352.10 (C₂₅H₁₇Cl = 352.86) Sub 1-A-78 m/z = 402.12 (C29H19Cl = 402.92) Sub 1-A-79 m/z = 352.10 (C₂₅H1₇Cl = 352.86) Sub 1-A-80 m/z = 472.08 (C₃₁H₂₁Br = 473.41) Sub 1-A-81 m/z = 550.13 (C₃₇H₂₇Br = 551.53) Sub 1-A-82 m/z = 548.11 (C₃₇H₂₅Br = 549.51) Sub 1-A-83 m/z = 472.08 (C₃₁H₂₁Br = 473.41) Sub 1-A-84 m/z = 585.09 (C₃₆H₂₂BrF₂N = 586.48 Sub 1-A-85 m/z = 394.04 (C₂₅H₁₅Br = 395.30) Sub 1-A-86 m/z = 350.09 (C₂₅H₁₅Cl = 350.85) Sub 1-A-87 m/z = 350.09 (C₂₅H₁₅Cl = 350.85) Sub 1-A-88 m/z = 470.07 (C₃₁H₁₉Br = 471.40) Sub 1-A-89 m/z = 470.07 (C₃₁H₁₉Br = 471.40) Sub 1-A-90 m/z = 470.07 (C₃₁H₁₉Br = 471.40) Sub 1-A-91 m/z = 470.07 (C₃₁H₁₉Br = 471.40) Sub 1-A-92 m/z = 504.03 (C₃₁H₁₈BrCl = 505.84) Sub 1-A-93 m/z = 470.07 (C₃₁H₁₉Br = 471.40) Sub 1-A-94 m/z = 546.10 (C₃₇H₂₃Br = 547.50) Sub 1-A-95 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-96 m/z = 476.13 (C₃₅H₂₁Cl = 477.00) Sub 1-A-97 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-98 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-99 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-100 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-101 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-102 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-103 m/z = 478.12 (C₃₃H₁₉ClN₂ = 478.98) Sub 1-A-104 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-105 m/z = 400.10 (C₂₈H₁₇Cl = 400.91) Sub 1-A-106 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-107 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-108 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-109 m/z = 526.15 (C₃₉H₂₃Cl = 527.06) Sub 1-A-110 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-111 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-112 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-113 m/z = 566.14 (C₄₁H₂₃ClO = 567.08) Sub 1-A-114 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-115 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-116 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-117 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-118 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-119 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-120 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-121 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-122 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-123 m/z = 425.10 (C₃₀H₁₆ClN = 425.92) Sub 1-A-124 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-125 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-126 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-127 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-128 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-129 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-130 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-131 m/z = 400.10 (C₂₉H₁₇Cl = 400.91) Sub 1-A-132 m/z = 520.08 (C₃₅H₂₁Br = 521.46) Sub 1-A-133 m/z = 520.08 (C₃₅H₂₁Br = 521.46) Sub 1-A-134 m/z = 520.08 (C₃₅H₂₁Br = 521.46) Sub 1-A-135 m/z = 510.09 (C₃₅H₂₀Cl₂ = 511.45) Sub 1-A-136 m/z = 610.09 (C₄₁H₂₃BrO = 611.54) Sub 1-A-137 m/z = 626.07 (C₄₁H₂₃BrS = 627.60) Sub 1-A-138 m/z = 636.15 (C₄₄H₂₉Br = 637.62) Sub 1-A-139 m/z = 450.12 (C₃₃H₁₉Cl = 450.97) Sub 1-A-140 m/z = 450.12 (C₃₃H₁₉Cl = 450.97) Sub 1-A-141 m/z = 500.13 (C₃₇H₂₁Cl = 501.03) Sub 1-A-142 m/z = 450.12 (C₃₃H₁₉Cl = 450.97) Sub 1-A-143 m/z = 450.12 (C₃₃H₁₉Cl = 450.97) Sub 1-A-144 m/z = 670.13 (C₄₇H₂₇Br = 671.64) Sub 1-A-145 m/z = 696.15 (C₄₉H₂₉Br = 697.68) Sub 1-A-146 m/z = 772.15 (C₅₃H₂₉BrN₂ = 773.73) Sub 1-A-148 m/z = 348.05 (C₂₁H₁₇Br = 349.27) Sub 1-A-149 m/z = 424.08 (C₂₇H₂₁Br = 425.37) Sub 1-A-152 m/z = 396.05 (C₂₅H₁₇Br = 397.32) Sub 1-A-154 m/z = 322.04 (C₁₉H₁₅Br = 323.23) Sub 1-A-155 m/z = 231.99 (C₁₂H₉Br = 233.11) Sub 1-A-156 m/z = 282 (C₁₆H₁₁Br = 283.17) Sub 1-A-157 m/z = 332.02 (C₂₀H₁₃Br = 333.23) Sub 1-A-161 m/z = 384.05 (C₂₄H₁₇Br = 385.3) Sub 1-A-162 m/z = 408.05 (C₂₆H₁₇Br = 409.33) Sub 1-A-163 m/z522.10 (C₃₅H₂₃Br = 523.47) Sub 1-A-164 m/z = 372.01 (C₂₂H₁₃BrO = 373.25) Sub 1-A-165 m/z = 387.99 (C₂₂H₁₃BrS = 389.31) Sub 1-A-166 m/z = 398.07 (C₂₅H₁₉Br = 399.33) Sub 1-A-167 m/z = 493.98 (C₂₈H₁₅BrS2 = 495.45) Sub 1-A-168 m/z = 514.13 (C₃₄H₂₇Br = 515.49) Sub 1-A-169 m/z = 478.00 (C₂₈H₁₅BrOS = 479.39) Sub 1-A-170 m/z = 493.98 (C₂₈H₁₅BrS₂ = 495.45) Sub 1-A-171 m/z = 474.10 (C₃₁H₂₃Br = 475.43) Sub 1-A-172 m/z = 478.00 (C₂₈H₁₅BrOS = 479.39) Sub 1-A-173 m/z = 387.99 (C₂₂H₁₃BrS = 389.31) Sub 1-A-b-1 m/z = 321.02 (C₁₈H₁₂BrN = 322.20) Sub 1-A-b-2 m/z = 397.05 (C₂₄H₁₆BrN = 398.29) Sub 1-A-b-3 m/z = 549.11 (C₃₆H₂₄BrN = 550.49) Sub 1-A-b-4 m/z = 550.10 (C₃₅H₂₃BrN₂ = 551.47) Sub 1-A-b-5 m/z = 473.08 (C₃₀H₂₀BrN = 474.39) Sub 1-A-b-6 m/z = 474.07 (C₂₉H₁₉BrN₂ = 475.38) Sub 1-A-b-7 m/z = 447.06 (C₂₈H₁₈BrN = 448.35) Sub 1-A-b-8 m/z = 447.06 (C₂₈H₁₈BrN = 448.35) Sub 1-A-b-9 m/z = 447.06 (C₂₈H₁₈BrN = 448.35) Sub 1-A-b-10 m/z = 497.08 (C₃₂H₂₀BrN = 498.41) Sub 1-A-b-11 m/z = 497.08 (C₃₂H₂₀BrN = 498.41) Sub 1-A-b-12 m/z = 397.05 (C₂₄H₁₆BrN = 398.29) Sub 1-A-b-13 m/z = 638.14 (C₄₂H₂₇BrN₂ = 639.58) Sub 1-A-b-14 m/z = 579.07 (C₃₆H₂₂BrNS = 580.54) Sub 1-A-b-15 m/z = 451.09 (C₂₈H₂₂BrN = 452.38) Sub 1-A-b-16 m/z = 564.12 (C₃₆H₂₅BrN₂ = 565.50) Sub 1-A-b-17 m/z = 447.06 (C₂₈H₁₈BrN = 448.35) Sub 1-A-b-18 m/z = 397.05 (C₂₄H₁₆BrN = 398.29) Sub 1-A-b-19 m/z = 397.05 (C₂₄H₁₆BrN = 398.29) Sub 1-A-b-20 m/z = 447.06 (C₂₈H₁₈BrN = 448.35) Sub 1-A-b-21 m/z = 497.08 (C₃₂H₂₀BrN = 498.41) Sub 1-A-b-22 m/z = 397.05 (C₂₄H₁₆BrN = 398.29) Sub 1-A-b-23 m/z = 397.05 (C₂₄H₁₆BrN = 398.29) Sub 1-A-b-24 m/z = 421.05 (C₂₆H₁₆BrN = 422.32) Sub 1-A-b-25 m/z = 447.06 (C₂₈H₁₈BrN = 448.35) Sub 1-A-b-26 m/z = 473.08 (C₃₀H₂₀BrN = 474.39) Sub 1-A-b-27 m/z = 625.14 (C₄₂H₂₈BrN = 626.58) Sub 1-A-b-28 m/z = 548.09 (C₃₅H₂₁BrN₂ = 549.46) Sub 1-A-b-29 m/z = 427.00 (C₂₄H₁₄BrNS = 428.34) Sub 1-A-b-30 m/z = 527.03 (C₃₂H₁₈BrNS = 528.46) Sub 1-A-b-31 m/z = 427.00 (C₂₄H₁₄BrNS = 428.34) Sub 1-A-b-32 m/z = 427.00 (C₂₄H₁₄BrNS = 428.34) Sub 1-A-b-33 m/z = 411.03 (C₂₄H₁₄BrNO = 412.28) Sub 1-A-b-34 m/z = 411.03 (C₂₄H₁₄BrNO = 412.28) Sub 1-A-b-35 m/z = 437.08 (C₂₇H₂₀BrN = 438.36) Sub 1-A-b-36 m/z = 563.12 (C₃₇H₂₆BrN = 564.51) Sub 1-A-b-37 m/z = 590.14 (C₃₈H₂₇BrN₂ = 591.54) Sub 1-A-b-38 m/z = 487.09 (C₃₁H₂₂BrN = 488.42) Sub 1-A-b-39 m/z = 487.09 (C₃₁H₂₂BrN = 488.42) Sub 1-A-b-40 m/z = 487.09 (C₃₁H₂₂BrN = 488.42) Sub 1-A-b-41 m/z = 537.11 (C₃₅H₂₄BrN = 538.48) Sub 1-A-b-42 m/z = 537.11 (C₃₅H₂₄BrN = 538.48) Sub 1-A-b-43 m/z = 437.08 (C₂₇H₂₀BrN = 438.36) Sub 1-A-b-44 m/z = 561.11 (C₃₇H₂₄BrN = 562.50) Sub 1-A-b-45 m/z = 561.11 (C₃₇H₂₄BrN = 562.50) Sub 1-A-b-46 m/z = 559.09 (C₃₇H₂₂BrN = 560.48) Sub 1-A-b-47 m/z = 559.09 (C₃₇H₂₂BrN = 560.48) Sub 1-A-b-48 m/z = 762.17 (C₅₂H₃₁BrN₂ = 763.72)

2. Example of Sub 1-B

Examples of Sub 1-B of Reaction Scheme 2 are as follows, but are not limited thereto. The same symbols as those used in Formula 1, Formula 1-A-1 to 1-A-5, and Formula 1-D-1 to 1-D-6 are defined identically, and b is an integer of 0 to 4 in Sub 1-B-b, y and z are each 0 or 1 and except when both are 1 in Sub 1-B-c, and m, l, etc. are each an integer of 0 to 4, r is an integer of 0 to 4, s is an integer of 0 to 3.

Synthesis of Sub 1-B-a to Sub 1-B-d

1. Synthesis Example of Sub 1-B-1

After diphenylamine (15.22 g, 89.94 mmol) was dissolved in toluene (750 ml), Sub 1-B-1-st (CAS Registry Number: 669773-34-6) (46.14 g, 134.91 mmol), Pd₂(dba)₃ (2.47 g, 2.70 mmol), P(t-Bu)₃ (1.82 g, 8.99 mmol) and NaOt-Bu (25.93 g, 269.81 mmol) were added to the solution and the mixture was stirred at 80° C. When the reaction was completed, the reaction product was extracted with CH₂Cl₂ and water. Then, an organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 23.61 g (yield: 61%) of the product.

2. Synthesis Example of Sub 1-B-63

After N-phenyldibenzo[b,d]furan-4-amine (10.94 g, 42.18 mmol) was dissolved in toluene (422 ml), Sub 1-B-63-st (10 g, 42.18 mmol), Pd₂(dba)₃ (1.16 g, 1.27 mmol) P(t-Bu)₃ (8.53 g, 42.18 mmol) and NaOt-Bu (8.11 g, 84.36 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of Sub 1-B-1 to obtain 13 g (yield: 67%) of the product.

3. Synthesis Example of Sub 1-B-157

After diphenylamine (25 g, 95 mmol) was dissolved in toluene (950 ml), Sub 3-157-st (16.08 g, 95 mmol), Pd₂(dba)₃ (2.61 g, 2.85 mmol) P(t-Bu)₃ (19.22 g, 95 mmol) and NaOt-Bu (18.26 g, 190 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of Sub 1-B-1 to obtain 24.45 g (yield: 65%) of the product.

Compounds belong to Sub 1-B are as follows, but are not limited thereto, and FD-MS values of the compounds are shown in Table 2 below.

TABLE 2 Compound FD-MS Compound FD-MS Sub 1-B-1 m/z = 429.02 (C₂₄H₁₆BrNS = 430.36) Sub 1-B-2 m/z = 413.04 (C₂₄H₁₆BrNO = 414.30) Sub 1-B-3 m/z = 463.06 (C₂₈H₁₈BrNO = 464.36) Sub 1-B-4 m/z = 385.07 (C₂₄H₁₆ClNS = 385.91) Sub 1-B-5 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-6 m/z = 567.09 (C₃₆H₂₂ClNS₂ = 568.15) Sub 1-B-7 m/z = 551.11 (C₃₆H₂₂ClNOS = 552.09) Sub 1-B-8 m/z = 501.13 (C₃₃H₂₄ClNS = 502.07) Sub 1-B-9 m/z = 445.12 (C₃₀H₂₀ClNO = 445.95) Sub 1-B-10 m/z = 445.12 (C₃₀H₂₀ClNO = 445.95) Sub 1-B-11 m/z = 385.07 (C₂₄H₁₆ClNS = 385.91) Sub 1-B-12 m/z = 491.06 (C₃₀H₁₈ClNS₂ = 492.05) Sub 1-B-13 m/z = 567.09 (C₃₆H₂₂ClNS₂ = 568.15) Sub 1-B-14 m/z = 541.07 (C₃₄H₂₀ClNS₂ = 542.11) Sub 1-B-15 m/z = 575.11 (C₃₈H₂₂ClNOS = 576.11) Sub 1-B-16 m/z = 552.11 (C₃₅H₂₁ClN₂OS = 553.08) Sub 1-B-17 m/z = 626.16 (C₄₂H₂₇ClN₂S = 627.20) Sub 1-B-18 m/z = 643.12 (C₄₂H₂₆ClNS₂ = 644.25) Sub 1-B-19 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-20 m/z = 369.09 (C₂₄H₁₆ClNO = 369.85) Sub 1-B-21 m/z = 475.08 (C₃₀H₁₈ClNOS = 475.99) Sub 1-B-22 m/z = 565.09 (C₃₆H₂₀ClNO₂S = 566.07) Sub 1-B-23 m/z = 519.14 (C₃₆H₂₂ClNO = 520.03) Sub 1-B-24 m/z = 385.07 (C₂₄H₁₆ClNS = 385.91) Sub 1-B-25 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-26 m/z = 567.09 (C₃₆H₂₂ClNS₂ = 568.15) Sub 1-B-27 m/z = 597.04 (C₃₆H₂₀ClNS₃ = 598.19) Sub 1-B-28 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-29 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-30 m/z = 485.10 (C₃₂H₂₀ClNS = 486.03) Sub 1-B-31 m/z = 591.14 (C₃₉H₂₆ClNOS = 592.15) Sub 1-B-32 m/z = 559.13 (C₃₈H₂₂ClNO₂ = 560.05) Sub 1-B-33 m/z = 677.16 (C₄₆H₂₈ClNOS = 678.25) Sub 1-B-34 m/z = 385.07 (C₂₄H₁₆ClNS = 385.91) Sub 1-B-35 m/z = 399.08 (C₂₅H₁₈ClNS = 399.94) Sub 1-B-36 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-37 m/z = 461.10 (C₃₀H₂₀ClNS = 462.01) Sub 1-B-38 m/z = 511.12 (C₃₄H₂₂ClNS = 512.07) Sub 1-B-39 m/z = 399.08 (C₂₅H₁₈ClNS = 399.94) Sub 1-B-40 m/z = 461.10 (C₃₀H₂₀ClNS = 462.01) Sub 1-B-41 m/z = 491.06 (C₃₀H₁₈ClNS₂ = 492.05) Sub 1-B-42 m/z = 491.06 (C₃₀H₁₈ClNS₂ = 492.05) Sub 1-B-43 m/z = 491.06 (C₃₀H₁₈ClNS₂ = 492.05) Sub 1-B-44 m/z = 541.07 (C₃₄H₂₀ClNS₂ = 542.11) Sub 1-B-45 m/z = 643.12 (C₄₂H₂₆ClNS₂ = 644.25) Sub 1-B-46 m/z = 607.12 (C₃₉H₂₆ClNS₂ = 608.21) Sub 1-B-47 m/z = 541.07 (C₃₄H₂₀ClNS₂ = 542.11) Sub 1-B-48 m/z = 475.08 (C₃₀H₁₈ClNOS = 475.99) Sub 1-B-49 m/z = 626.16 (C₄₂H₂₇ClN₂S = 627.20) Sub 1-B-50 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-51 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-52 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-53 m/z = 541.07 (C₃₄H₂₀ClNS₂ = 542.11) Sub 1-B-54 m/z = 555.09 (C₃₅H₂₂ClNS₂ = 556.14) Sub 1-B-55 m/z = 525.10 (C₃₄H₂₀ClNOS = 526.05) Sub 1-B-56 m/z = 513.13 (C₃₄H₂₄ClNS = 514.08) Sub 1-B-57 m/z = 485.10 (C₃₂H₂₀ClNS = 486.03) Sub 1-B-58 m/z = 537.13 (C₃₆H₂₄ClNS = 538.11) Sub 1-B-59 m/z = 626.16 (C₄₂H₂₇ClN₂S = 627.20) Sub 1-B-60 m/z = 369.09 (C₂₄H₁₆ClNO = 369.85) Sub 1-B-61 m/z = 445.12 (C₃₀H₂₀ClNO = 445.95) Sub 1-B-62 m/z = 495.14 (C₃₄H₂₂ClNO = 496.01) Sub 1-B-63 m/z = 459.10 (C₃₀H₁₈ClNO₂ = 459.93) Sub 1-B-64 m/z = 534.15 (C₃₆H₂₃ClN₂O = 535.04) Sub 1-B-65 m/z = 535.17 (C₃₇H₂₆ClNO = 536.07) Sub 1-B-66 m/z = 525.10 (C₃₄H₂₀ClNOS = 526.05) Sub 1-B-67 m/z = 385.07 (C₂₄H₁₆ClNS = 385.91) Sub 1-B-68 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-69 m/z = 461.10 (C₃₀H₂₀ClNS = 462.01) Sub 1-B-70 m/z = 611.15 (C₄₂H₂₆ClNS = 612.19) Sub 1-B-71 m/z = 567.09 (C₃₆H₂₂ClNS₂ = 568.15) Sub 1-B-72 m/z = 541.07 (C₃₄H₂₀ClNS₂ = 542.11) Sub 1-B-73 m/z = 475.08 (C₃₀H₁₈ClNOS = 475.99) Sub 1-B-74 m/z = 551.11 (C₃₆H₂₂ClNOS = 552.09) Sub 1-B-75 m/z = 591.14 (C₃₉H₂₆ClNOS = 592.15) Sub 1-B-76 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-77 m/z = 591.09 (C₃₈H₂₂ClNS₂ = 592.17) Sub 1-B-78 m/z = 537.13 (C₃₆H₂₄ClNS = 538.11) Sub 1-B-79 m/z = 379.15 (C₂₄H₆D₁₀ClNO = 379.91) Sub 1-B-80 m/z = 459.10 (C₃₀H₁₈ClNO₂ = 459.93) Sub 1-B-81 m/z = 445.12 (C₃₀H₂₀ClNO = 445.95) Sub 1-B-82 m/z = 429.02 (C₂₄H₁₆BrNS = 430.36) Sub 1-B-83 m/z = 443.03 (C₂₅H₁₈BrNS = 444.39) Sub 1-B-84 m/z = 479.03 (C₂₈H₁₈BrNS = 480.42) Sub 1-B-85 m/z = 485.10 (C₃₂H₂₀ClNS = 486.03) Sub 1-B-86 m/z = 545.12 (C₃₄H₂₄ClNO₂S = 546.08) Sub 1-B-87 m/z = 413.04 (C₂₄H₁₆BrNO = 414.30) Sub 1-B-88 m/z = 529.10 (C₃₃H₂₄BrNO = 530.47) Sub 1-B-89 m/z = 589.10 (C₃₈H₂₄BrNO = 590.52) Sub 1-B-90 m/z = 385.07 (C₂₄H₁₆ClNS = 385.91) Sub 1-B-91 m/z = 537.13 (C₃₆H₂₄ClNS = 538.11) Sub 1-B-92 m/z = 491.06 (C₃₀H₁₈ClNS₂ = 492.05) Sub 1-B-93 m/z = 567.09 (C₃₆H₂₂ClNS₂ = 568.15) Sub 1-B-94 m/z = 567.09 (C₃₆H₂₂ClNS₂ = 568.15) Sub 1-B-95 m/z = 551.11 (C₃₆H₂₂ClNOS = 552.09) Sub 1-B-96 m/z = 683.15 (C₄₅H₃₀ClNS₂ = 684.31) Sub 1-B-97 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-98 m/z = 591.09 (C₃₈H₂₂ClNS₂ = 592.17) Sub 1-B-99 m/z = 748.18 (C₄₉H₃₃ClN₂S₂ = 749.39) Sub 1-B-100 m/z = 369.09 (C₂₄H₁₆ClNO = 369.85) Sub 1-B-101 m/z = 419.11 (C₂₈H₁₈ClNO = 419.91) Sub 1-B-102 m/z = 475.08 (C₃₀H₁₈ClNOS = 475.99) Sub 1-B-103 m/z = 625.13 (C₄₂H₂₄ClNOS = 626.17) Sub 1-B-104 m/z = 429.02 (C₂₄H₁₆BrNS = 430.36) Sub 1-B-105 m/z = 479.03 (C₂₈H₁₈BrNS = 480.42) Sub 1-B-106 m/z = 505.05 (C₃₀H₂₀BrNS = 506.46) Sub 1-B-107 m/z = 435.08 (C₂₈H₁₈ClNS = 435.97) Sub 1-B-108 m/z = 541.07 (C₃₄H₂₀ClNS₂ = 542.11) Sub 1-B-109 m/z = 489.07 (C₃₀H₂₀BrNO = 490.40) Sub 1-B-110 m/z = 565.10 (C₃₆H₂₄BrNO = 566.50) Sub 1-B-111 m/z = 716.15 (C₄₇H₂₉BrN₂O = 717.67) Sub 1-B-112 m/z = 385.07 (C₂₄H₁₆ClNS = 385.91) Sub 1-B-113 m/z = 511.12 (C₃₄H₂₂ClNS = 512.07) Sub 1-B-114 m/z = 557.14 (C₃₅H₂₈ClNSSi = 558.21) Sub 1-B-115 m/z = 495.14 (C₃₄H₂₂ClNO = 496.01) Sub 1-B-116 m/z = 575.11 (C₃₈H₂₂ClNOS = 576.11) Sub 1-B-117 m/z = 469.12 (C₃₂H₂₀ClNO = 469.97) Sub 1-B-118 m/z = 469.12 (C₃₂H₂₀ClNO = 469.97) Sub 1-B-119 m/z = 635.17 (C₄₄H₂₆ClNO₂ = 636.15) Sub 1-B-120 m/z = 650.16 (C₄₄H₂₇ClN₂S = 651.22) Sub 1-B-121 m/z = 585.13 (C₄₀H₂₄ClNS = 586.15) Sub 1-B-122 m/z = 673.08 (C₄₂H₂₄ClNS₃ = 674.29) Sub 1-B-123 m/z = 491.06 (C₃₀H₁₈ClNS₂ = 492.05) Sub 1-B-124 m/z = 461.1 (C₃₀H₂₀ClNS = 462.01) Sub 1-B-125 m/z = 641.16 (C₄₃H₂₈ClNOS = 642.21) Sub 1-B-126 m/z = 445.16 (C₃₁H₂₄ClN = 445.99) Sub 1-B-127 m/z = 471.18 (C₃₃H₂₆ClN = 472.03) Sub 1-B-128 m/z = 395.14 (C₂₇H₂₂ClN = 395.93) Sub 1-B-129 m/z = 471.18 (C₃₃H₂₆ClN = 472.03) Sub 1-B-130 m/z = 395.14 (C₂₇H₂₂ClN = 395.93) Sub 1-B-131 m/z = 511.21 (C₃₆H₃₀ClN = 512.09) Sub 1-B-132 m/z = 423.18 (C₂₉H₂₆ClN = 423.98) Sub 1-B-133 m/z = 569.19 (C₄₁H₂₈ClN = 570.13) Sub 1-B-134 m/z = 595.21 (C₄₃H₃₀ClN = 596.17) Sub 1-B-135 m/z = 519.18 (C₃₇H₂₆ClN = 520.07) Sub 1-B-136 m/z = 567.18 (C₄₁H₂₆ClN = 568.12) Sub 1-B-137 m/z = 515.14 (C₃₇H₂₂ClN = 516.04) Sub 1-B-138 m/z = 517.16 (C₃₇H₂₄ClN = 518.06) Sub 1-B-139 m/z = 607.17 (C₄₃H₂₆ClNO = 608.14) Sub 1-B-140 m/z = 517.16 (C₂₇H₂₄ClN = 518.06) Sub 1-B-141 m/z = 607.17 (C₄₃H₂₆ClNO = 608.14) Sub 1-B-142 m/z = 395.14 (C₂₇H₂₂ClN = 395.93) Sub 1-B-143 m/z = 485.15 (C₃₃H₂₄ClNO = 486.01) Sub 1-B-148 m/z = 507.18 (C₃₆H₂₆ClN = 508.06) Sub 1-B-149 m/z = 457.16 (C₃₂H₂₄ClN = 458) Sub 1-B-150 m/z = 519.18 (C₃₇H₂₆ClN = 520.07) Sub 1-B-161 m/z = 399.06 (C₂₄H₁₈BrN = 400.32) Sub 1-B-162 m/z = 449.08 (C₂₈H₂₀BrN = 450.38) Sub 1-B-163 m/z = 499.09 (C₃₂H₂₂BrN = 500.44) Sub 1-B-164 m/z = 475.09 (C₃₀H₂₂BrN = 476.42) Sub 1-B-165 m/z = 480.12 (C₃₀H₁₇D₅BrN = 481.45) Sub 1-B-166 m/z = 525.11 (C₃₄H₂₄BrN = 526.48) Sub 1-B-167 m/z = 575.12 (C₃₈H₂₆BrN = 576.54) Sub 1-B-169 m/z = 551.12 (C₃₆H₂₆BrN = 552.52) Sub 1-B-171 m/z = 616.15 (C₄₀H₂₉BrN₂ = 617.59) Sub 1-B-178 m/z = 627.16 (C₄₂H₃₀BrN = 628.61) Sub 1-B-182 m/z = 489.07 (C₃₀H₂₀BrNO = 490.4) Sub 1-B-184 m/z = 555.07 (C₃₄H₂₂BrNS = 556.52) Sub 1-B-185 m/z = 657.11 (C₄₁H₂BrNS = 658.66) Sub 1-B-186 m/z = 591.16 (C₃₉H₃₀BrN = 592.58) Sub 1-B-187 m/z = 631.19 (C₄₂H₃₄BrN = 632.65) Sub 1-B-188 m/z = 505.05 (C₃₀H₂₀BrNS = 506.46) Sub 1-B-190 m/z = 581.08 (C₃₆H₂₄BrNS = 582.56) Sub 1-B-193 m/z = 611.04 (C₃₆H₂₂BrNS₂ = 612.6) Sub 1-B-194 m/z = 631.1 (C₄₀H₂₆BrNS = 632.62) Sub 1-B-204 m/z = 539.09 (C₃₄H₂₂BrNO = 540.46) Sub 1-B-206 m/z = 615.12 (C₄₀H₂₆BrNO = 616.56) Sub 1-B-209 m/z = 641.14 (C₄₂H₂₈BrNO = 642.6) Sub 1-B-211 m/z = 565.14 (C₃₇H₂₈BrN = 566.54) Sub 1-B-212 m/z = 591.16 (C₃₉H₃₀BrN = 592.58)

2. Synthesis Example of Sub 2

Sub 2 of Reaction Schemes 1 and 2 may be synthesized by the reaction route of Reaction Scheme 6 below, but is not limited thereto.

Synthesis of Sub 2-1

After bromobenzene (37.1 g, 236.2 mmol) was dissolved in toluene (2200 mL), aniline (20 g, 214.8 mmol), Pd₂(dba)₃ (9.83 g, 10.7 mmol), P(t-Bu)₃ (4.34 g, 21.5 mmol) and NaOt-Bu (62 g, 644.3 mmol) were added sequentially the solution and the mixture was stirred at 100° C. When the reaction was completed, the reaction product was extracted with ether and water. Then, an organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 28 g (yield: 77%) of the product.

Synthesis of Sub 2-80

After [1,1′-biphenyl]-4-amine (15 g, 88.64 mmol) was dissolved in toluene (886 mL), 2-bromodibenzo[b,d]thiophene (23.32 g, 88.64 mmol), Pd₂(dba)₃ (2.43 g, 2.66 mmol), P(t-Bu)₃ (17.93 g, 88.64 mmol) and NaOt-Bu (17.04 g, 177.27 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of Sub 2-1 to obtain 24.61 g (yield: 79%) of the product.

Synthesis of Sub 2-134

After [1,1′-biphenyl]-4-amine (15 g, 88.6 mmol) was dissolved in toluene (931 mL), 2-(4-bromophenyl)-9,9-diphenyl-9H-fluorene (46.2 g, 97.5 mmol), Pd₂(dba)₃ (4.06 g, 4.43 mmol), P(t-Bu)₃ (1.8 g, 8.86 mmol) and NaOt-Bu (28.1 g, 292.5 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of Sub 2-1 to obtain 34.9 g (yield: 70%) of the product.

Synthesis of Sub 2-222

After 3-bromonaphtho[2,3-b]benzofuran (15 g, 50.48 mmol) was dissolved in toluene (505 mL), [1,1′-biphenyl]-4-amine (8.54 g, 50.48 mmol), Pd₂(dba)₃ (1.39 g, 1.51 mmol), P(t-Bu)₃ (10.21 g, 50.48 mmol) and NaOt-Bu (9.70 g, 100.96 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of Sub 2-1 to obtain 13.82 g (yield: 71%) of the product.

Compounds belong to Sub 2 are as follows, but are not limited thereto, and FD-MS values of the compounds are shown in Table 3 below.

TABLE 3 Compound FD-MS Compound FD-MS Sub 2-1 m/z = 169.09(C₁₂H₁₁N = 169.22) Sub 2-2 m/z = 245.12(C₁₈H₁₅N = 245.32) Sub 2-3 m/z = 245.12(C₁₈H₁₅N = 245.32) Sub 2-4 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-5 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-6 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 2-7 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 2-8 m/z = 295.14(C₂₂H_(l7)N = 295.38) Sub 2-9 m/z = 409.18(C₃₁H₂₃N = 409.52) Sub 2-10 m/z = 483.20(C₃₇H₂₅N = 483.60) Sub 2-11 m/z = 459.20(C₃₅H₂₅N = 459.58) Sub 2-12 m/z = 485.21(C₃₇H₂₇N = 485.62) Sub 2-13 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-14 m/z = 335.13(C₂₄H₁₇NO = 335.40) Sub 2-15 m/z = 297.13(C₂₀H_(l5)N₃ = 297.35) Sub 2-16 m/z = 219.10(C_(l6)H_(l3)N = 219.28) Sub 2-17 m/z = 249.12(C₁₇H₁₅NO = 249.31) Sub 2-18 m/z = 197.12(C₁₄H₁₅N = 197.28) Sub 2-19 m/z = 229.11(C₁₄H₁₅NO₂ = 229.27) Sub 2-20 m/z = 174.12(C₁₂H₆D₅N = 174.25) Sub 2-21 m/z = 281.21(C₂₀H₂₇N = 281.44) Sub 2-22 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-23 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-24 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-25 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-26 m/z = 321.15(C₂₄H_(l9)N = 321.41) Sub 2-27 m/z = 297.13(C₂₀H₁₅N₃ = 297.35) Sub 2-28 m/z = 499.20(C₃₆H₂₅N₃ = 499.60) Sub 2-29 m/z = 499.20(C₃₆H₂₂N₂ = 410.51) Sub 2-30 m/z = 424.16(C₃₀H₂₀N₂O = 424.49) Sub 2-31 m/z = 440.13(C₃₀H₂₀N₂S = 440.56) Sub 2-32 m/z = 384.16(C_(2S)H₂₀N₂ = 384.47) Sub 2-33 m/z = 334.15(C₂₄H_(1s)N₂ = 334.41) Sub 2-34 m/z = 450.21(C₃₃H₂₆N₂ = 450.57) Sub 2-35 m/z = 410.18(C₃₀H₂₂N₂ = 410.51) Sub 2-36 m/z = 410.18(C_(3O)H₂₂N₂ = 410.51) Sub 2-37 m/z = 575.24(C₄₂H₂₉N₃ = 575.70) Sub 2-38 m/z = 574.24(C₄₃H₃₀N₂ = 574.71) Sub 2-39 m/z = 460.19(C₃₄H₂₄N₂ = 460.57) Sub 2-40 m/z = 460.19(C₃₄H₂₄N₂ = 460.57) Sub 2-41 m/z = 461.19(C₃₃H₂₃N₃ = 461.56) Sub 2-42 m/z = 626.27(C₄₇H₃₄N₂ = 626.79) Sub 2-43 m/z = 565.23(C₃₉H₂₇N₅ = 565.67) Sub 2-44 m/z = 415.21(C₃₀H_(l7)D₅N₂ = 415.54) Sub 2-45 m/z = 486.21(C₃₆H₂₆N₂ = 486.61) Sub 2-46 m/z = 415.21(C₃₀H_(l7)D₅N₂ = 415.54) Sub 2-47 m/z = 225.15(C₁₆H₁₉N = 225.33) Sub 2-48 m/z = 220.10(C₁₅H₁₂N₂ = 220.27) Sub 2-49 m/z = 220.10(C₁₅H₁₂N₂ = 220.27) Sub 2-50 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 2-51 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 2-52 m/z = 293.12(C₂₂H₁₅N = 293.36) Sub 2-53 m/z = 250.1 5(C₁₈H₁₀D₅N = 250.35) Sub 2-54 m/z = 250.15(C_(1s)H₁₀D₅N = 250.35) Sub 2-55 m/z = 246.12(C₁₇H₁₄N₂ = 246.31) Sub 2-56 m/z = 295.14(C₂₂H₁₇N = 295.38) Sub 2-57 m/z = 295.14(C₂₂H₁₇N = 295.38) Sub 2-58 m/z = 295.14(C₂₂H₁₇N = 295.38) Sub 2-59 m/z = 300.17(C₂₂H_(l2)D₅N = 300.41) Sub 2-60 m/z = 295.14(C₂₂H₁₇N = 295.38) Sub 2-61 m/z = 295.14(C₂₂H₁₇N = 295.38) Sub 2-62 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 2-63 m/z = 345.15(C₂₆H₁₉N = 345.44) Sub 2-64 m/z = 296.13(C₂₁H₁₆N₂ = 296.37) Sub 2-65 m/z = 346.15(C₂₅H₁₈N = 346.42) Sub 2-66 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-67 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-68 m/z = 421.18(C₃₂H₂₃N = 421.53) Sub 2-69 m/z = 300.17(C₂₂H₁₂D₅N = 300.41) Sub 2-70 m/z = 421.18(C₃₂H₂₃N = 421.53) Sub 2-71 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-72 m/z = 371.17(G₂₈H₂₁N = 371.47) Sub 2-73 m/z = 319.14(C₂₄H₁₇N = 319.40) Sub 2-74 m/z = 293.12(C₂₂H₁₅N = 293.36) Sub 2-75 m/z = 395.17(C₃₀H₂₁N = 395.49) Sub 2-76 m/z = 386.18(C₂₈H₂₂N2 = 386.49) Sub 2-77 m/z = 224.14(C₁₆H₈D₅N = 224.31) Sub 2-78 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-79 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-80 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-81 m/z = 351.11(C₂₄H₁₇NS = 351.46) Sub 2-82 m/z = 326.09(C₂₁H₁₄N₂S = 326.41) Sub 2-83 m/z = 351.11(C₂₄H₁₇NS = 351.46) Sub 2-84 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-85 m/z = 290.09(C₁₈H₁₄N₂S = 290.38) Sub 2-86 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-87 m/z = 351.11(C₂₄H₁₇NS = 351.46) Sub 2-88 m/z = 381.06(C₂₄H₁₅NS₂ = 381.51) Sub 2-89 m/z = 401.12(C₂₈H₁₉NS = 401.52) Sub 2-90 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-91 m/z = 351.11(C₂₄H₁₇NS = 351.46) Sub 2-92 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-93 m/z = 401.12(C₂₈H₁₉NS = 401.52) Sub 2-94 m/z = 351.11(C₂₄H₁₇NS = 351.46) Sub 2-95 m/z = 352.10(C₂₃H₁₆N₂S = 352.45) Sub 2-96 m/z = 440.13(C₃₀H₂₀N₂S = 440.56) Sub 2-97 m/z = 375.11(C₂₆H₁₇NS = 375.48) Sub 2-98 m/z = 381.06(C₂₄H₁₅NS₂ = 381.51) Sub 2-99 m/z = 351.11(C₂₄H₁₇NS = 351.46) Sub 2-100 m/z = 309.12(C₂₂H₁₅NO = 309.36) Sub 2-101 m/z = 259.10(C₁₈H₁₃NO = 259.30) Sub 2-102 m/z = 309.12(C₂₂H₁₅NO = 309.36) Sub 2-103 m/z = 335.13(C₂₄H₁₇NO = 335.40) Sub 2-104 m/Z = 349.11(C₂₄H₁₅NO₂ = 349.38) Sub 2-105 m/z = 309.12(C₂₂H₁₅NO = 309.36) Sub 2-106 m/z = 259.10(C₁₈H₁₃NO = 259.30) Sub 2-107 m/z = 335.13(C₂₄H₁₇NO = 335.40) Sub 2-108 m/z = 259.10(C₁₈H₁₃NO = 259.30) Sub 2-109 m/z = 335.13(C₂₄H₁₇NO = 335.40) Sub 2-110 m/z = 461.18(C₃₄H₂₃NO = 461.55) Sub 2-111 m/z = 335.13(C₂₄H₁₇NO = 335.40) Sub 2-112 m/z = 335.13(C₂₄H₁₇NO = 335.40) Sub 2-113 m/z = 335.13(C₂₄Hi₇NO = 335.40) Sub 2-114 m/z = 385.15(C₂₈H₁₉NO = 385.46) Sub 2-115 m/z = 411.16(C₃₀H₂₁NO = 411.49) Sub 2-116 m/z = 411.16(C₃₀H₂₁NO = 411.49) Sub 2-117 m/z = 285.15(C₂₁H₁₉N = 285.38) Sub 2-118 m/z = 290.18(C₂₁H₁₄D_(s)N = 290.41) Sub 2-119 m/z = 335.17(C₂₅H₂₁N = 335.44) Sub 2-120 m/z = 361.18(C₂₇H₂₃N = 361.48) Sub 2-121 m/z = 391.14(C₂₇H₂₁NS = 391.53) Sub 2-122 m/z = 401.21(C₃₀H₂₇N = 401.54) Sub 2-123 m/z = 335.17(C₂₅H₂₁N = 335.44) Sub 2-124 m/z = 335.17(C₂₅H₂₁N = 335.44) Sub 2-125 m/z = 385.18(C₂₉H₂₃N = 385.50) Sub 2-126 m/z = 361.18(C₂₇H₂₃N = 361.48) Sub 2-127 m/z = 299.17(C₂₂H₂₁N = 299.41) Sub 2-128 m/z = 385.18(C₂₉H₂₃N = 385.50) Sub 2-129 m/z = 409.18(C₃₁H₂₃N = 409.52) Sub 2-130 m/z = 525.25(C₄₀H₃₁N = 525.68) Sub 2-131 m/z = 409.18(C₃₁H₂₃N = 409.52) Sub 2-132 m/z = 423.20(C₃₂H₂₅N = 423.55) Sub 2-133 m/z = 439.19(C₃₂H₂₅NO = 439.5 5) Sub 2-134 m/z = 459.20(C₃₅H₂₅N = 459.58) Sub 2-135 m/z = 485.21(C₃₇H₂₇N = 485.62) Sub 2-136 m/z = 562.24(C₄₂H₃₀N₂ = 562.70) Sub 2-137 m/z = 485.21(C₃₇H₂₇N = 485.62) Sub 2-138 m/z = 523.23(C₄₀H₂₉N = 523.66) Sub 2-139 m/z = 407.17(C₃₁H₂₁N = 407.51) Sub 2-140 m/z = 407.17(C₃₁H₂₁N = 407.51) Sub 2-141 m/z = 483.20(C₃₇H₂₅N = 483.60) Sub 2-142 m/z = 457.18(C_(3S)H₂₃N = 457.56) Sub 2-143 m/z = 410.18(C₃₀H₂₂N₂ = 410.51) Sub 2-144 m/z = 384.16(C₂₈H₂₀N₂ = 384.47) Sub 2-145 m/z = 384.16(C₂₈H₂₀N₂ = 384.47) Sub 2-146 m/z = 410.18(C₃₀H₂₂N₂ = 410.51) Sub 2-147 m/z = 450.21(C₃₃H₂₆N₂ = 450.57) Sub 2-148 m/z = 384.16(C₂₈H₂₀N₂ = 384.47) Sub 2-149 m/z = 225.06(C₁₄H₁₁NS = 225.31) Sub 2-150 m/z = 225.06(C₁₄H₁₁NS = 225.31) Sub 2-151 m/z = 284.13(C₂₀H₁₆N₂ = 284.35) Sub 2-152 m/z = 334.15(C₂₄H_(l8)N₂ = 334.41) Sub 2-153 m/z = 293.07(C₁₈H₁₂FNS = 293.36) Sub 2-154 m/z = 220.10(C₁₅H₁₂N₂ = 220.27) Sub 2-155 m/z = 297.13(C₂₀H₁₅N₃ = 297.35) Sub 2-156 m/z = 245.12(C₁₈H₁₅N = 245.32) Sub 2-157 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-158 m/z = 349.11(C₂₄H₁₅NO₂ = 349.38) Sub 2-159 m/z = 365.09(C₂₄H₁₅NOS = 365.45) Sub 2-160 m/z = 365.09(C₂₄H₁₅NOS = 365.45) Sub 2-161 m/z = 365.09(C₂₄H₁₅NOS = 365.45) Sub 2-162 m/z = 365.09(C₂₄H₁₅NOS = 365.45) Sub 2-163 m/z = 415.10(C₂₈H₁₇NOS = 415.51) Sub 2-164 m/z = 365.09(C₂₄H₁₅NOS = 365.45) Sub 2-165 m/z = 465.12(C₃₂ H₁₉NOS = 465.57) Sub 2-166 m/z = 391.14(C₂₇H₂₁NS = 391.53) Sub 2-167 m/z = 391.14(C₂₇H₂₁NS = 391.53) Sub 2-168 m/z = 515.17(C₃₇H₂₅NS = 515.67) Sub 2-169 m/z = 513.16(C₃₇H₂₃NS = 513.65) Sub 2-170 m/Z = 375.16(C₂₇H₂₁NO = 375.46) Sub 2-171 m/z = 497.18(C₃₇H₂₃NO = 497.58) Sub 2-172 m/z = 477.25(C_(3S)H₃₁N = 477.64) Sub 2-173 m/z = 561.25(C₄₃H₃₁N = 561.73) Sub 2-174 m/z = 411.2(C₃₁H₂₅N = 411.55) Sub 2-175 m/z = 475.19(C_(3S)H₂₅NO = 475.59) Sub 2-176 m/z = 575.22(C₄₃H₂₉NO = 575.71) Sub 2-177 m/z = 533.21(C₄₁H₂₇N = 533.67) Sub 2-178 m/z = 499.19(C₃₇H₂₅NO = 499.61) Sub 2-179 m/z = 439.19(C₃₂H₂₅NO = 439.56) Sub 2-180 m/z = 400.17(C₂₇H₂₀N₄ = 400.49) Sub 2-181 m/z = 399.17(C₂₈H₂₁N₃ = 399.5) Sub 2-182 m/z = 427.14(C₃₀H₂₁NS₂ = 427.57) Sub 2-183 m/z = 461.18(C₃₄H₂₃NO = 461.56) Sub 2-184 m/z = 381.06(C₂₄H₁₅NS₂ = 381.51) Sub 2-185 m/z = 457.1(C₃₀H₁₉NS₂ = 457.61) Sub 2-186 m/z = 533.13(C₃₆H₂₃NS₂ = 533.71) Sub 2-187 m/z = 375.11(C₂₆H₁₇NS = 375.49) Sub 2-188 m/z = 411.16(C₃₀H₂₁NO = 411.5) Sub 2-189 m/z = 425.14(C₃₀H₁₉NO₂ = 425.49) Sub 2-190 m/z = 475.16(C₃₄H₂₁NO₂ = 475.55) Sub 2-191 m/z = 327.08(C₂₀H₁₃N₃S = 327.41) Sub 2-192 m/z = 353.1(C₂₂H₁₅N₃S = 353.44) Sub 2-193 m/z = 455.26(C₃₄H₃₃N = 455.65) Sub 2-194 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-195 m/z = 515.17(C₃₇H₂₅NS = 515.67) Sub 2-196 m/z = 515.17(C₃₇H₂₅NS = 515.67) Sub 2-197 m/z = 467.17(C33H25NS = 467.63) Sub 2-198 m/z = 259.1(C₁₈H₁₃NO = 259.31) Sub 2-199 m/z = 485.22(C₃₄H₃₁NS = 485.69) Sub 2-200 m/z = 220.10(C₁₅H₁₂N₂ = 220.28) Sub 2-201 m/z = 246.12(C17H14N2 = 246.31) Sub 2-202 m/z = 220.10(C₁₅H₁₂N₂ = 220.28) Sub 2-203 m/z = 376.19(C27H24N2 = 376.50) Sub 2-204 m/z = 375.20(C₂₈H₂₅N = 375.52) Sub 2-205 m/z = 366.21(C₂₇H₁₈D₅N = 366.52) Sub 2-206 m/z = 411.20(C₃₁H₂₅N = 411.55) Sub 2-207 m/z = 361.18(C₂₇H₂₅N = 361.49) Sub 2-208 m/z = 411.20(C₃₁H₂₅N = 411.55) Sub 2-209 m/z = 361.18(C₂₇H₂₃N = 361.49) Sub 2-210 m/z = 361.18(C₂₇H₂₃N = 361.49) Sub 2-211 m/z = 334.15(C₂₄H₁₈N₂ = 334.42) Sub 2-212 m/z = 486.21(C₃₆H₂₆N₂ = 486.62) Sub 2-213 m/z = 486.21(C₃₆H₂₆N₂ = 486.62) Sub 2-214 m/z = 332.13(C₂₄ H₁₆N₂ = 332.41) Sub 2-215 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-216 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-217 m/z = 259.10(C₁₈H₁₃NO = 259.31) Sub 2-218 m/z = 375.16(C₂₇H₂₁NO = 375.47) Sub 2-219 m/z = 411.16(C₃₀H₂₁NO = 411.50) Sub 2-220 m/z = 411.16(C₃₀H₂₁NO = 411.50) Sub 2-221 m/z = 461.18(C₃₄H₂₃NO = 461.56) Sub 2-222 m/z = 385.15(C₂₈H₁₉NO = 385.47) Sub 2-223 m/z = 523.23(C₄₀H₂₉N = 523.68)

A synthesis example of Final Product 1 of Reaction Scheme 1 is as follows.

Synthesis Example of Final Products 1 Synthesis of 1-54

1) Synthesis of Inter_A-1

After N-phenyl[1,1′-biphenyl]-4-amine (11.6 g, 47.3 mmol) was dissolved in toluene (500 mL), 2-(3,5-dibromophenyl)-9-phenyl-9H-carbazole (24.8 g, 52.0 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol) and NaOt-Bu (13.6 g, 141.8 mmol) were added to the solution and the mixture was stirred at 100° C. When the reaction was completed, the reaction product was extracted with CH₂Cl₂ and water. Then, an organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 22.8 g (yield: 75%) of the product.

2) Synthesis of 1-54

After N-phenyldibenzo[b,d]thiophen-2-amine (8 g, 29.05 mmol) was dissolved in toluene (305 mL), Inter_A-1 (20.5 g, 32 mmol), Pd₂(dba)₃ (1.5 g, 1.6 mmol), P(t-Bu)₃ (0.65 g, 3.2 mmol) and NaOt-Bu (8.4 g, 87.2 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of Inter_A-1 to obtain 18g (yield: 74%) of the product 1-54.

Synthesis of 2-9

After Sub 2-26 (7 g, 21.8 mmol) was dissolved in toluene (230 mL), Sub 1-2 (9.54 g, 24 mmol), Pd₂(dba)₃ (1 g, 1.1 mmol), 50% P(t-Bu)₃ (1.1 ml, 2.2 mmol) and NaOt-Bu (6.91 g, 71.9 mmol) were added to the solution and the mixture was stirred at 100° C. When the reaction was completed, the reaction product was extracted with CH₂Cl₂ and water. Then, an organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 11.69 g (yield: 84%) of the product.

Synthesis of 3-52

After 2-bromonaphtho[2,3-b]benzofuran (10 g, 33.65 mmol) was dissolved in toluene (337 mL), N-([1,1′-biphenyl]-4-yl)dibenzo[b,d]thiophen-2-amine (11.83 g, 33.65 mmol), Pd₂(dba)₃ (0.92 g, 1.01 mmol), P(t-Bu)₃ (6.81 g, 33.65 mmol) and NaOt-Bu (6.47 g, 67.31 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of 2-9 to obtain 15.28 g (yield: 80%) of the product.

Synthesis of 6-12

After 2-bromo-11,11-dimethyl-11H-benzo[b]fluorene (10 g, 30.94 mmol) was dissolved in toluene (309 mL), N-([1,1′-biphenyl]-4-yl)naphtho[2,3-b]benzofuran-3-amine (11.93 g, 30.94 mmol), Pd₂(dba)₃ (0.85 g, 0.93 mmol), P(t-Bu)₃ (6.26 g, 30.94 mmol) and NaOt-Bu (5.95 g, 61.88 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of 2-9 to obtain 15.15 g (yield: 78%) of the product.

Synthesis of 11-4

After 1-(4-bromophenyl)naphthalene (10 g, 35.3 mmol) was dissolved in toluene (353 mL), bis(4-(naphthalen-1-yl)phenyl)amine (14.8 g, 35.31 mmol), Pd₂(dba)₃ (0.97 g, 1.06 mmol), P(t-Bu)₃ (7.14 g, 35.31 mmol) and NaOt-Bu (6.79 g, 70.63 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of 2-9 to obtain 16.9 g (yield: 78%) of the product.

[Synthesis Example of 1-2] Synthesis Example of Compounds (Final Product 1′) Represented by Formula 1

Some compounds of the present invention were prepared by the synthesis method disclosed in Korean Patent No. 10-1668448 (registration-published on Oct. 17, 2016) and Korean Patent Registration No. 10-1789998 (registration-published on Oct. 19, 2017) of the present applicant.

1. Synthesis Example of 7-8

After 7-bromo-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (8 g, 18.2 mmol) was dissolved in toluene (100 ml), N-phenyldibenzo[b,d]thiophen-2-amine (5 g, 18.2 mmol), Pd₂(dba)₃ (0.5 g, 0.55 mmol) P(t-Bu)₃ (0.23 g, 1.1 mmol) and NaOt-Bu (5.3 g, 54.6 mmol) were added to the solution and the mixture was stirred at 100° C. When the reaction was completed, the reaction product was extracted with CH₂Cl₂ and water. Then, an organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 8.9 g (yield: 76%) of the product.

2. Synthesis Example of 10-37

After 8-bromo-N,N-diphenyldibenzo[b,d]thiophen-3-amine (5.29 g, 12.29 mmol) was dissolved in toluene (125 ml), N-([1,1′-biphenyl]-4-yl)dibenzo[b,d]thiophen-2-amine (4.32 g, 12.29 mmol), Pd₂(dba)₃ (0.34 g, 0.37 mmol) P(t-Bu)₃ (0.25 g, 1.23 mmol) and NaOt-Bu (3.54 g, 36.87 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of 7-8 to obtain 6.81 g (yield: 79%) of the product.

3. Synthesis Example of 10-176

After 9-chloro-N-(dibenzo[b,d]thiophen-3-yl)-N-phenyl-[2,4′-bidibenzo[b,d]thiophen]-1′-amine (25 g, 37.08 mmol) was dissolved in toluene (371 ml), diphenylamine (6.27 g, 37.08 mmol), Pd₂(dba)₃ (1.02 g, 1.11 mmol) P(t-Bu)₃ (7.50 g, 37.08 mmol) and NaOt-Bu (7.13 g, 74.15 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of 7-8 to obtain 8.9 g (yield: 72%) of the product.

4. Synthesis Example of 12-1

After N-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine (25 g, 55.51 mmol) was dissolved in toluene (555 ml), diphenylamine (9.39 g, 55.51 mmol), Pd₂(dba)₃ (1.52 g, 1.67 mmol) P(t-Bu)₃ (11.23 g, 55.51 mmol), NaOt-Bu (10.67 g, 111.02 mmol) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of 7-8 to obtain 21.77 g (yield: 81%) of the product.

FD-MS values of the compounds 1-1 to 12-70 of the present invention synthesized by the above synthesis method are shown in Table 4 below.

TABLE 4 Compound FD-MS Compound FD-MS 1-1  m/z = 562.24(C₄₂H₃₀N₂ = 562.72) 1-2  m/z = 602.27(C₄₅H₃₄N₂ = 602.78) 1-3  m/z = 563.24(C₄₁H₂₉N₃ = 563.70) 1-4  m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 1-5  m/z = 678.30(C₅₁H₃₈N₂ = 678.88) 1-6  m/z = 802.33(C₆₁H₄₂N₂ = 803.02) 1-7  m/z = 800.32(C₆₁H₄₀N₂ = 801.01) 1-8  m/z = 563.24(C₄₁H₂₉N₃ = 563.70) 1-9  m/z = 668.23(C₄₈H₃₂N₂S = 668.86) 1-10 m/z = 727.30(C₅₄H₃₇N₃ = 727.91) 1-11 m/z = 652.25(C₄₈H₃₂N₂O = 652.80) 1-12 m/z = 662.27(C₅₀H₃₄N₂ = 662.84) 1-13 m/z = 536.23(C₄₀H₂₈N₂ = 536.68) 1-14 m/z = 586.24(C₄₄H₃₀N₂ = 586.74) 1-15 m/z = 712.29(C₅₄H₃₆N₂ = 712.90) 1-16 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 1-17 m/z = 754.33(C₅₇H₄₂N₂ = 754.98) 1-18 m/z = 957.38(C₇₀H₄₇N₅ = 958.18) 1-19 m/z = 965.38(C₇₃H₄₇N₃ = 966.20) 1-20 m/z = 719.24(C₅₁H₃₃N₃S = 719.91) 1-21 m/z = 758.24(C₅₄H₃₄N₂OS = 758.94) 1-22 m/z = 893.38(C₆₇H₄₇N₃ = 894.13) 1-23 m/z = 652.25(C₄₈H₃₂N₂O = 652.80) 1-24 m/z = 662.27(C₅₀H₃₄N₂ = 662.84) 1-25 m/z = 562.24(C₄₂H₃₀N₂ = 562.72) 1-26 m/z = 612.26(C₄₆H₃₂N₂ = 612.78) 1-27 m/z = 688.29(C₅₂H₃₆N₂ = 688.87) 1-28 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 1-29 m/z = 754.33(C₅₇H₄₂N₂ = 754.98) 1-30 m/z = 878.37(C₆₇H₄₆N₂ = 879.12) 1-31 m/z = 876.35(C₆₇H₄₄N₂ = 877.10) 1-32 m/z = 639.27(C₄₇H₃₃N₃ = 369.80) 1-33 m/z = 768.26(C₅₆H₃₆N₂S = 768.98) 1-34 m/z = 833.29(C₆₀H₃₉N₃S = 834.05) 1-35 m/z = 742.26(C₅₄H₃₄N₂O₅ = 742.88) 1-36 m/z = 778.333(C₅₉H₄₂N₂ = 779.00) 1-37 m/z = 486.21 (C₃₆H₂₆N₂ = 486.62) 1-38 m/z = 536.23(C₄₀H₂₈N₂ = 536.68) 1-39 m/z = 612.26(C₄₆H₃₂N₂ = 612.78) 1-40 m/z = 638.27(C₄₈H₃₄N₂ = 638.81) 1-41 m/z = 491.24(C₃₆H₂₁D₅N₂ = 491.65) 1-42 m/z = 612.26(C₄₆H₃₂N₂ = 612.78) 1-43 m/z = 794.28(C₅₈H₃₈N₂S = 795.02) 1-44 m/z = 656.26(C₄₈H₃₃FN₂ = 656.80) 1-45 m/z = 717.29(C₅₁H₃₅N₅ = 717.88) 1-46 m/z = 728.32(C₅₅H₄₀N₂ = 728.94) 1-47 m/z = 842.34(C₆₂H₄₂N₄ = 843.05) 1-48 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 1-49 m/z = 653.28(C₄₈H₃₅N₃ = 653.81) 1-50 m/z = 703.30(C₅₂H₃₇N₃ = 703.87) 1-51 m/z = 805.35(C₆₀H₄₃N₃ = 806.00) 1-52 m/z = 753.31(C₅₆H₃₉N₃ = 753.93) 1-53 m/z = 818.34(C₆₀H₄₂N₄ = 819.00) 1-54 m/z = 835.30(C₆₀H₄₁N₃S = 836.05) 1-55 m/z = 655.27(C₄₆H₃₃N₅ = 655.79) 1-56 m/z = 885.32(C₆₄H₄₃N₃S = 886.11) 1-57 m/z = 759.27(C₅₄H₃₇N₃S = 759.96) 1-58 m/z = 706.28(C₄₉H₃₄N₆ = 706.83) 1-59 m/z = 960.39(C₆₉H₄₈N₆ = 961.16) 1-60 m/z = 853.35(C₆₄H₄₃N₃ = 854.05) 1-61 m/z = 894.37(C₆₆H₄₆N₄ = 895.10) 1-62 m/z = 834.38(C₆₂H₃₈D₅N₃ = 835.06) 1-63 m/z = 855.36(C₆₄H₄₅N₅ = 856.06) 1-64 m/z = 853.35(C₅₄H₄₃N₃ = 854.05) 1-65 m/z = 794.37(C₆₀H₄₆N₂ = 795.04) 1-66 m/z = 987.39(C₇₁H₄₉N₅O = 988.21) 1-67 m/z = 1021.44(C₇₇H_(5S)N₃ = 1022.31) 1-68 m/z = 737.23(C₅₁H₃₂FN₃S = 737.90) 1-69 m/z = 562.24(C₄₂H₃₀N₂ = 562.72) 1-70 m/z = 602.27(C₄₅H₃₄N₂ = 602.78) 1-71 m/z = 563.24(C₄₁H₂₉N₃ = 563.70) 1-72 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 1-73 m/z = 678.30(C₅₁H₃₈N₂ = 678.88) 1-74 m/z = 802.33(C₆₁H₄₂N₂ = 803.02) 1-75 m/z = 800.32(C₆₁H₄₀N₂ = 801.01) 1-76 m/z = 563.24(C₄₁H₂₉N₃ = 563.70) 1-77 m/z = 668.23(C₄₈H₃₂N₂S = 668.86) 1-78 m/z = 727.30(C₅₄H₃₇N₃ = 727.91) 1-79 m/z = 652.25(C₄₈H₃₂N₂O = 652.80) 1-80 m/z = 662.27(C₅₀H₃₄N₂ = 662.84) 1-81 m/z = 536.23(C₄₀H₂₈N₂ = 536.68) 1-82 m/z = 586.24(C₄₄H₃₀N₂ = 586.74) 1-83 m/z = 712.29(C₅₄H₃₆N₂ = 712.90) 1-84 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 1-85 m/z = 754.33(C₅₇H₄₂N₂ = 754.98) 1-86 m/z = 957.38(C₇₀H₄₇N₅ = 958.18) 1-87 m/z = 965.38(C₇₃H₄₇N₃ = 966.20) 1-88 m/z = 719.24(C₅₁H₃₃N₃S = 719.91) 1-89 m/z = 758.24(C₅₄H₃₄N₂OS = 758.94) 1-90 m/z = 893.38(C₆₇H₄₇N₃ = 894.13) 1-91 m/z = 652.25(C₄₈H₃₂N₂O = 652.80) 1-92 m/z = 662.27(C₅₀H₃₄N₂ = 662.84) 1-93 m/z = 562.24(C₄₂H₃₀N₂ = 562.72) 1-94 m/z = 612.26(C₄₆H₃₂N₂ = 612.78) 1-95 m/z = 688.29(C₅₂H₃₆N₂ = 688.87) 1-96 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 1-97 m/z = 754.33(C₅₇H₄₂N₂ = 754.98) 1-98 m/z = 878.37(C₆₇H₄₆N₂ = 879.12) 1-99 m/z = 876.35(C₆₇H₄₄N₂ = 877.10)  1-100 m/z = 639.27(C₄₇H₃₃N₃ = 369.80)  1-101 m/z = 768.26(C₅₆H₃₆N₂S = 768.98)  1-102 m/z = 833.29(C₆₀H₃₉N₃S = 834.05)  1-103 m/z = 742.26(C₅₄H₃₄N₂O₅ = 742.88)  1-104 m/z = 778.333(C₅₉H₄₂N₂ = 779.00)  1-105 m/z = 486.21(C₃₆H₂₆N₂ = 486.62)  1-106 m/z = 536.23(C₄₀H₂₈N₂ = 536.68)  1-107 m/z = 612.26(C₄₆H₃₂N₂ = 612.78)  1-108 m/z = 638.27(C₄₈H₃₄N₂ = 638.81)  1-109 m/z = 491.24(C₃₅H₂₁D₅N₂ = 491.65)  1-110 m/z = 612.26(C₄₆H₃₂N₂ = 612.78)  1-111 m/z = 794.28(C₅₈H₃₈N₂S = 795.02)  1-112 m/z = 656.26(C₄₈H₃₃FN₂ = 656.80)  1-113 m/z = 717.29(C₅₁H₃₅N₅ = 717.88)  1-114 m/z = 728.32(C₅₅H₄₀N₂ = 728.94)  1-115 m/z = 842.34(C₆₂H₄₂N₄ = 843.05)  1-116 m/z = 714.30(C₅₄H₃₈N₂ = 714.91)  1-117 m/z = 653.28(C₄₈H₃₅N₃ = 653.81)  1-118 m/z = 703.30(C₅₄H₃₈N₃ = 703.87)  1-119 m/z = 805.35(C₆₀H₄₃N₃ = 806.00)  1-120 m/z = 753.31(C₅₆H₃₉N₃ = 753.93)  1-121 m/z = 818.34(C₆₀H₄₂N₄ = 819.00)  1-122 m/z = 835.30(C₆₀H₄₁N₃S = 836.05)  1-123 m/z = 655.27(C₄₆H₃₃N₅ = 655.79)  1-124 m/z = 885.32(C₆₄H₄₃N₃S = 886.11)  1-125 m/z = 759.27(C₅₄H₃₇N₃S = 759.96)  1-126 m/z = 706.28(C₄₉H₃₄N₆ = 706.83)  1-127 m/z = 960.39(C₆₉H₄₈N₆ = 961.16)  1-128 m/z = 853.35(C₆₄H₄₃N₃ = 854.05)  1-129 m/z = 894.37(C₆₅H₄₆N₄ = 895.10)  1-130 m/z = 834.38(C₆₂H₃₈D₅N₃ = 835.06)  1-131 m/z = 855.36(C₆₄H₄₅N₃ = 856.06)  1-132 m/z = 853.35(C₆₄H₄₃N₃ = 854.05)  1-133 m/z = 794.37(C₆₀H₄₆N₂ = 795.04)  1-134 m/z = 987.39(C₇₁H₄₉N₅O = 988.21)  1-135 m/z = 1021.44(C₇₇H₅₅N₃ = 1022.31)  1-136 m/z = 737.23(C₅₁H₃₂FN₃S = 737.90)  1-137 m/z = 650.27(C₄₉H₃₄N₂ = 650.83) 2-1  m/z = 486.21(C₃₆H₂₆N₂ = 486.61) 2-2  m/z = 541.26(C₄₀H₂₃D₅N₂ = 541.69) 2-3  m/z = 612.26(C₄₅H₃₂N₂ = 612.76) 2-4  m/z = 562.24(C₄₂H₃₀N₂ = 562.70) 2-5  m/z = 636.26(C₄₈H₃₂N₂ = 636.78) 2-6  m/z = 586.24(C₄₄H₃₀N₂ = 586.72) 2-7  m/z = 712.29(C₅₄H₃₆N₂ = 712.88) 2-8  m/z = 638.27(C₄₈H₃₄N₂ = 638.80) 2-9  m/z = 638.27(C₄₈H₃₄N₂ = 638.80) 2-10 m/z = 638.27(C₄₈H₃₄N₂ = 638.80) 2-11 m/z = 638.27(C₄₈H₃₄N₂ = 638.80) 2-12 m/z = 738.30(C₅₆H₃₈N₂ = 738.91) 2-13 m/z = 653.28(C₄₈H₃₅N₃ = 653.B1) 2-14 m/z = 820.36(C₆₀H₄₄N₄ = 821.02) 2-15 m/z = 651.27(C₄₈H₃₃N₃ = 651.80) 2-16 m/z = 642.21(C₄₆H₃₀N₂S = 642.81) 2-17 m/z = 668.23(C₄₈H₃₂N₂S = 668.85) 2-18 m/z = 668.23(C₄₈H₃₂N₂S = 668.85) 2-19 m/z = 692.23(C₅₀H₃₂N₂S = 692.87) 2-20 m/z = 708.26(C₅₁H₃₆N₂S = 708.91) 2-21 m/z = 794.28(C₅₈H₃₂N₂S = 795.00) 2-22 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) 2-23 m/z = 652.25(C₄₈H₃₂N₂O = 652.78) 2-24 m/z = 778.30(C₅₈H₃₈N₂O = 778.94) 2-25 m/z = 753.28(C₅₅H₃₅N₃O = 753.89) 2-26 m/z = 666.23(C₄₈H₃₀N₂O₂ = 666.76) 2-27 m/z = 682.21(C₄₈H₃₀N₂OS = 682.83) 2-28 m/z = 682.21(C₄₈H₃₀N₂OS = 682-83) 2-29 m/z = 678.30(C₅₁H₃₈N₂ = 678.86) 2-30 m/z = 702.30(C₅₃H₃₈N₂ = 702.88) 2-31 m/z = 692.28(C₅₁H₃₆N₂O = 692.84) 2-32 m/z = 708.26(C₅₁H₃₆N₂S = 708.91) 2-33 m/z = 794.37(C₆₀H₄₆N₂ = 795.02) 2-34 m/z = 802.33(C₆₁H₄₂N₂ = 803.00) 2-35 m/z = 879.36(C₆₅H₄₅N₃ = 880.08) 2-36 m/z = 842.37(C₆₄H₄₆N₂ = 843.06) 2-37 m/z = 832.29(C₆₁H₄₀N₂S = 833.05) 2-38 m/z = 724.29(C₅₅H₃₆N₂ = 724.89) 2-39 m/z = 800.32(C₆₁H₄₀N₂ = 800.98) 2-40 m/z = 840.35(C₆₄H₄₄N₂ = 841.05) 2-41 m/z = 830.28(C₆₁H₃₈N₂S = 831.03) 2-42 m/z = 814.30(C₆₁H₃₈N₂O = 814.97) 2-43 m/z = 638.27(C₄₈H₃₄N₂ = 638.80) 2-44 m/z = 803.33(C₆₀H₄₁N₃ = 803.99) 2-45 m/z = 638.27(C₄₈H₃₄N₂ = 638.80) 2-46 m/z = 668.23(C₄₈H₃₂N₂S = 668.85) 2-47 m/z = 678.30(C₄₈H₃₄N₂ = 678.86) 2-48 m/z = 835.30(C₆₀H₄₁N₃S = 836.05) 2-49 m/z = 682.21(C₄₈H₃₀N₂OS = 682.83) 2-50 m/z = 668.23(C₄₈H₃₂N₂S = 668.85) 2-51 m/z = 612.26(C₄₅H₃₂N₂ = 612.76) 2-52 m/z = 638.27(C₄₈H₃₄N₂ = 638.80) 2-53 m/z = 782.24(C₅₆H₃₄N₂OS = 782.95) 2-54 m/z = 790.33(C₆₀H₄₂N₂ = 790.99) 2-55 m/z = 805.31(C₅₉H₃₉N₃O = 805.96) 2-56 m/z = 664.29(C₅₀H₃₆N₂ = 664.83) 2-57 m/z = 803.33(C₆₀H₄₁N₃ = 803.99) 2-58 m/z = 768.26(C₅₆H₃₆N₂S = 768.96) 2-59 m/z = 650.27(C₄₉H₃₄N₂ = 650.81) 2-60 m/z = 688.29(C₅₂H₃₆N₂ = 688.86) 2-61 m/z = 744.26(C₅₄H₃₆N₂S = 744.94) 2-62 m/z = 667.21(C₄₇H₂₉N₃S = 667.82) 2-63 m/z = 642.21(C₄₆H₃₀N₂S = 642.81) 2-64 m/z = 566.18(C₄₀H₂₆N₂S = 566.71) 2-65 m/z = 699.18(C₄₇H₂₉N₃S₂ = 699.88) 2-66 m/z = 682.21(C₄₈H₃₀N₂OS = 682.83) 2-67 m/z = 742.24(C₅₄H₃₄N₂S = 742.93) 2-68 m/z = 652.25(C₄₈H₃₂N₂O = 652.78) 2-69 m/z = 652.25(C₄₈H₃₂N₂O = 652.78) 2-70 m/z = 678.30(C₅₁H₃₈N₂ = 678.86) 2-71 m/z = 657.32(C₄₉H₃₁D₅N₂ = 657.85) 2-72 m/z = 576.26(C₄₃H₃₂N₂ = 576.73) 2-73 m/z = 642.30(C₄₈H₃₈N₂ = 642.83) 2-74 m/z = 766.33(C₅₈H₄₂N₂ = 766.97) 2-75 m/z = 767.33(C₅₇H₄₁N₃ = 767.96) 2-76 m/z = 708.26(C₅₁H₃₆N₂S = 708.91) 2-77 m/z = 692.28(C₅₁H₃₆N₂O = 692.84) 2-78 m/z = 706.26(C₅₁H₃₄N₂O₂ = 706.83) 2-79 m/z = 722.24(C₅₁H₃₄N₂OS = 722.89) 2-80 m/z = 666.27(C₄₉H₃₄N₂O = 666.81) 2-81 m/z = 603.27(C₄₄H₃₃N₃ = 603.75) 2-82 m/z = 778.33(C₅₉H₄₂N₂ = 778.98) 2-83 m/z = 755.33(C₅₆H₄₁N₃ = 755.94) 2-84 m/z = 802.33(C₆₁H₄₂N₂ = 803.00) 2-85 m/z = 778.31(C₅₇H₃₈N₄ = 778.94) 2-86 m/z = 890.37(C₆₈H₄₆N₂ = 891.11) 2-87 m/z = 756.26(C₅₅H₃₆N₂S = 756.95) 2-88 m/z = 846.27(C₆₁H₃₈N₂OS = 847.03) 2-89 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) 2-90 m/z = 648.26(C₄₉H₃₂N₂ = 648.79) 2-91 m/z = 800.32(C₆₁H₄₀N₂ = 800.98) 2-92 m/z = 830.28(C₆₁H₃₈N₂S = 831.03) 2-93 m/z = 864.31(C₆₅H₄₀N₂O = 865.03) 2-94 m/z = 840.35(C₆₄H₄₄N₂ = 841.05) 2-95 m/z = 936.35(C₇₂H₄₄N₂ = 937.13) 2-96 m/z = 844.25(C₆₁H₃₆N₂OS = 845.02) 2-97 m/z = 927.36(C₇₀H₄₅N₃ = 928.13) 2-98 m/z = 688.29(C₅₂H₃₆N₂ = 688.86) 2-99 m/z = 652.29(C₄₉H₃₅N₂ = 652.82)  2-100 m/z = 826.33(C₆₃H₄₂N₂ = 827.02)  2-101 m/z = 702.27(C₅₂H₃₄N₂O = 702.84)  2-102 m/z = 688.29(C₅₂H₃₆N₂ = 688.86)  2-103 m/z = 728.32(C₅₅H₄₀N₂ = 728.92)  2-104 m/z = 884.29(C₆₄H₄₀N₂OS = 885.08)  2-105 m/z = 586.24(C₄₄H₃₀N₂ = 586.72)  2-106 m/z = 718.24(C₅₂H₃₄N₂S = 718.90)  2-107 m/z = 732.22(C₅₂H₃₂N₂OS = 732.89)  2-108 m/z = 702.30(C₅₃H₃₈N₂ = 702.88)  2-109 m/z = 688.29(C₅₂H₃₆N₂ = 688.86)  2-110 m/z = 702.27(C₅₂H₃₄N₂O = 702.84)  2-111 m/z = 692.23(C₅₀H₃₂N₂S = 692.87)  2-112 m/z = 782.24(C₅₆H₃₄N₂OS = 782.95)  2-113 m/z = 738.30(C₅₆H₃₈N₂ = 738.91)  2-114 m/z = 768.26(C₅₆H₃₆N₂S = 768.96)  2-115 m/z = 716.32(C₅₄H₄₀N₂ = 716.91)  2-116 m/z = 857.29(C₆₂H₃₉N₃S = 858.06)  2-117 m/z = 738.30(C₅₆H₃₈N₂ = 738.91)  2-118 m/z = 753.28(C₅₅H₃₅N₃O = 753.89)  2-119 m/z = 677.28(C₅₀H₃₅N₃ = 677.83)  2-120 m/z = 879.32(C₆₅H₄₁N₃O = 880.04)  2-121 m/z = 612.26(C₄₆H₃₂N₂ = 612.76)  2-122 m/z = 756.31(C₅₆H₄₀N₂O = 756.93)  2-123 m/z = 727.30(C₅₄H₃₇N₃ = 727.89)  2-124 m/z = 866.37(C₆₆H₄₆N₂ = 867.08) 3-1  m/z = 503.17(C₃₆H₂₅NS = 503.66) 3-2  m/z = 603.20(C₄₄H₂₉NS = 603.77) 3-3  m/z = 477.16(C₃₄H₂₃NS = 477.62) 3-4  m/z = 503.17(C₃₆H₂₅NS = 503.66) 3-5  m/z = 451.14(C₃₂H₂₁NS = 451.58) 3-6  m/z = 593.22(C₄₃H₃₁NS = 593.78) 3-7  m/z = 641.22(C₄₇H₃₁NS = 641.82) 3-8  m/z = 665.22(C₄₉H₃₁NS = 665.84) 3-9  m/z = 503.17(C₃₆H₂₅NS = 503.66) 3-10 m/z = 655.23(C₄₈H₃₃NS = 655.85) 3-11 m/z = 695.26(C₅₁H₃₇NS = 695.91) 3-12 m/z = 593.18(C₄₂H₂₇NOS = 593.73) 3-13 m/z = 583.14(C₄₀H₂₅NS₂ = 583.76) 3-14 m/z = 579.20(C₄₂H₂₉NS = 579.75) 3-15 m/z = 685.19(C₄₈H₃₁NS₂ = 685.90) 3-16 m/z = 719.23(C₅₂H₃₃NOS = 719.89) 3-17 m/z = 629.22(C₄₆H₃₁NS = 629.81) 3-18 m/z = 629.22(C₄₆H₃₁NS = 629.81) 3-19 m/z = 603.20(C₄₄H₂₉NS = 603.77) 3-20 m/z = 563.08(C₃₆H₂₁NS₃ = 563.75) 3-21 m/z = 639.11(C₄₂H₂₅NS₃ = 639.85) 3-22 m/z = 715.15(C₄₈H₂₉NS₃ = 715.95) 3-23 m/z = 791.18(C₅₄H₃₃NS₃ = 792.04) 3-24 m/z = 607.16(C₄₂H₂₅NO₂S = 607.72) 3-25 m/z = 633.21(C₄₅H₃₁NOS = 633.80) 3-26 m/z = 733.24(C₅₃H₃₅NOS = 733.92) 3-27 m/z = 883.29(C₆₅H₄₁NOS = 884.09) 3-28 m/z = 585.13(C₃₈H₂₃N₃S₂ = 585.74) 3-29 m/z = 553.19(C₄₀H₂₇NS = 553.71) 3-30 m/z = 603.20(C₄₄H₂₉NS = 603.77) 3-31 m/z = 841.28(C₆₃H₃₉NS = 842.06) 3-32 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 3-33 m/z = 563.22(C₄₂H₂₉NO = 563.69) 3-34 m/z = 563.22(C₄₂H₂₉NO = 563.69) 3-35 m/z = 613.24(C₄₆H₃₁NO = 613.74) 3-36 m/z = 703.29(C₅₃H₃₇NO = 703.87) 3-37 m/z = 587.22(C₄₄H₂₉NO = 587.71) 3-38 m/z = 639.26(C₄₈H₃₃NO = 639.78) 3-39 m/z = 639.26(C₄₈H₃₃NO = 639.78) 3-40 m/z = 653.24(C₄₈H₃₁NO₂ = 653.77) 3-41 m/z = 603.26(C₄₅H₃₃NO = 603.75) 3-42 m/z = 727.29(C₅₅H₃₇NO = 727.89) 3-43 m/z = 725.27(C₅₅H₃₅NO = 725.87) 3-44 m/z = 595.17(C₄₀H₂₅N₃OS = 595.71) 3-45 m/z = 567.26(C₄₂H₃₃NO = 567.72) 3-46 m/z = 611.22(C₄₆H₂₉NO = 611.73) 3-47 m/z = 617.18(C₄₄H₂₇NOS = 617.76) 3-48 m/z = 637.24(C₄₈H₃₁NO = 637.77) 3-49 m/z = 667.21(C₄₈H₂₉NO₃ = 667.75) 3-50 m/z = 767.25(C₅₆H₃₃NO₃ = 767.87) 3-51 m/z = 681.27(C₅₀H₃₅NO₂ = 681.82) 3-52 m/z = 567.17(C₄₀H₂₅NOS = 567.71 3-53 m/z = 658.22(C₄₅H₃₀N₄S = 658.82) 3-54 m/z = 655.23(C₄₈H₃₃NS = 655.86) 3-55 m/z = 744.26(C₅₄H₃₅N₂S = 744.96) 3-56 m/z = 784.27(C₅₅H₃₆N₄S = 784.98) 3-57 m/z = 553.19(C₄₀H₂₇NS = 553.72) 3-58 m/z = 553.19(C₄₀H₂₇NS = 553.72) 3-59 m/z = 543.2(C₃₉H₂₉NS = 543.73) 3-60 m/z = 671.21(C₄₈H₃₀FNS = 671.83) 3-61 m/z = 641.25(C₄₆H₃₁N₃O = 641.77) 3-62 m/z = 639.26(C₄₈H₃₃NO = 639.8) 3-63 m/z = 652.25(C₄₈H₃₂N₂O = 652.8) 3-64 m/z = 667.25(C₄₉H₃₃NO₂ = 667.81) 3-65 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 3-66 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 3-67 m/z = 731.23(C₅₃H₃₃NOS = 731.91) 3-68 m/z = 731.23(C₅₃H₃₃NOS = 731.91) 3-69 m/z = 683.23(C₄₉H₃₃NOS = 683.87) 3-70 m/z = 551.19(C₄₀H₂₅NO₂ = 551.65) 3-71 m/z = 643.2(C₄₆H₂₉NOS = 643.8) 3-72 m/z = 601.2(C₄₄H₂₇NO₂ = 601.71) 3-73 m/z = 607.2(C₄₃H₂₉NOS = 607.77) 3-74 m/z = 701.28(C₅₀H₃₉NOS = 701.93) 3-75 m/z = 577.24(C₄₃H₃₁NO = 577.73) 3-76 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 4-1  m/z = 513.25(C₃₉H₃₁N = 513.68) 4-2  m/z = 613.28(C₄₇H₃₅N = 613.80) 4-3  m/z = 665.31(C₅₁H₃₉N = 665.88) 4-4  m/z = 705.34(C₅₄H₄₃N = 705.95) 4-5  m/z = 593.31(C₄₅H₃₉N = 593.81) 4-6  m/z = 589.28(C₄₅H₃₅N = 589.78) 4-7  m/z = 513.25(C₃₉H₃₁N = 513.68) 4-8  m/z = 639.29(C₄₉H₃₇N = 639.84) 4-9  m/z = 589.28(C₄₅H₃₅N = 589.78) 4-10 m/z = 665.31(C₅₁H₃₉N = 665.88) 4-11 m/z = 553.28(C₄₂H₃₅N = 553.75) 4-12 m/z = 669.34(C₅₁H₄₃N = 669.91) 4-13 m/z = 779.36(C₆₀H₄₅N = 780.03) 4-14 m/z = 761.35(C₅₆H₄₇NSi = 762.08) 4-15 m/z = 705.34(C₅₄H₄₃N = 705.95) 4-16 m/z = 589.28(C₄₅H₃₅N = 589.78) 4-17 m/z = 665.31(C₅₁H₃₉N = 665.88) 4-18 m/z = 728.3 2(C₅₅H₄₀N2 = 728.94) 4-19 m/z = 637.28(C₄₉H₃₅N = 637.83) 4-20 m/z = 789.34(C₆₁H₄₃N = 790.02) 4-21 m/z = 677.31(C₅₂H₃₉N = 677.89) 4-22 m/z = 775.32(C₆₀H₄₁N = 776.00) 4-23 m/z = 801.34(C₆₂H₄₃N = 802.03) 4-24 m/z = 799.32(C₆₂H₄₁N = 800.02) 4-25 m/z = 965.40(C₇₅H₅₁N = 966.24) 4-26 m/z = 637.28(C₄₉H₃₅N = 637.83) 4-27 m/z = 635.26(C₄₉H₃₃N = 635.81) 4-28 m/z = 616.29(C₄₇H₂₈D₅N = 616.82) 4-29 m/z = 727.32(C₅₆H₄₁N = 727.95) 4-30 m/z = 687.29(C₅₃H₃₇N = 687.89) 4-31 m/z = 877.37(C₆₈H₄₇N = 878.13) 4-32 m/z = 753.34(C₅₈H₄₃N = 753.99) 4-33 m/z = 689.31(C₅₃H₃₉N = 689.90) 4-34 m/z = 637.28(C₄₉H₃₅N = 637.83) 4-35 m/z = 850.32(C₅₂H₄₀F₂N₂ = 851.01) 4-36 m/z = 559.23(C₄₃H₂₉N = 559.71) 4-37 m/z = 635.26(C₄₉H₃₃N = 635.81) 4-38 m/z = 663.29(C₅₁H₃₇N = 663.86) 4-39 m/z = 735.29(C₅₇H₃₇N = 735.93) 4-40 m/z = 735.29(C₅₇H₃₇N = 735.93) 4-41 m/z = 725.31(C₅₆H₃₉N = 725.94) 4-42 m/z = 735.29(C₅₇H₃₇N = 735.93) 4-43 m/z = 751.32(C₅₈H₄₁N = 751.97) 4-44 m/z = 725.31(C₅₆H₃₉N = 725.94) 4-45 m/Z = 675.29(C₅₂H₃₇N = 675.88) 4-46 m/z = 675.29(C₅₂H₃₇N = 675.88) 4-47 m/z = 751.32(C₅₈H₄₁N = 751.97) 4-48 m/z = 675.29(C₅₂H₃₇N = 675.88) 4-49 m/z = 721.28(C₅₆H₃₅N = 721.90) 4-50 m/z = 797.31(C₆₂H₃₉N = 798.00) 4-51 m/z = 959.36(C₇₅H₄₅N = 960.19) 4-52 m/z = 607.23(C₄₇H₂₉N = 607.76) 4-53 m/z = 675.29(C₅₂H₃₇N = 675.88) 4-54 m/z = 635.26(C₄₉H₃₃N = 635.81) 4-55 m/z = 640.29(C₄₉H₂₈D₅N = 640.84) 4-56 m/z = 685.28(C₅₃H₃₅N = 685.87) 4-57 m/z = 735.29(C₅₇H₃₇N = 735.93) 4-58 m/z = 583.23(C₄₅H₂₉N = 583.73) 4-59 m/z = 725.31(C₅₆H₃₉N = 725.94) 4-60 m/z = 725.31(C₅₆H₃₉N = 725.94) 4-61 m/z = 635.26(C₄₉H₃₃N = 635.81) 4-62 m/z = 751.32(C₅₈H₄₁N = 751.97) 4-63 m/z = 751.32(C₅₈H₄₁N = 751.97) 4-64 m/z = 751.32(C₅₈H₄₁N = 751.97) 4-65 m/z = 842.37(C₆₄H₄₆N2 = 843.09) 4-66 m/z = 751.32(C₅₈H₄₁N = 751.97) 4-67 m/z = 873.34(C₆₈H₄₃N = 874.10) 4-68 m/z = 711.29(C₅₅H₃₇N = 711.91) 4-69 m/z = 751.32(C₅₈H₄₁N = 751.97) 4-70 m/z = 787.32(C₆₁H₄₁N = 788.01) 5-1  m/z = 583.23(C₄₅H₂₉N = 583.73) 5-2  m/z = 609.25(C₄₇H₃₁N = 609.77) 5-3  m/z = 685.28(C₅₃H₃₅N = 685.87) 5-4  m/z = 659.26(C₅₁H₃₃N = 659.83) 5-5  m/z = 607.23(C₄₇H₂₉N = 607.76) 5-6  m/z = 685.28(C₅₃H₃₅N = 685.87) 5-7  m/z = 664.29(C₅₁H₂₈D₅N = 664.86) 5-8  m/z = 649.28(C₅₀H₃₅N = 649.84) 5-9  m/z = 699.29(C₅₄H₃₇N = 699.90) 5-10 m/z = 699.29(C₅₄H₃₇N = 699.90) 5-11 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-12 m/z = 739.32(C₅₇H₄₁N = 739.96) 5-13 m/z = 730.34(C₅₆H₃₄D₅N = 730.97) 5-14 m/z = 775.32(C₆₀H₄₁N = 776.00) 5-15 m/z = 775.32(C₆₀H₄₁N = 776.00) 5-16 m/z = 775.32(C₆₀H₄₁N = 776.00) 5-17 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-18 m/z = 773.31(C₆₀H₃₉N = 773.98) 5-19 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-20 m/z = 774.30(C₅₉H₃₈N₂ = 774.97) 5-21 m/z = 639.20(C₄₇H₂₉NS = 639.82) 5-22 m/z = 699.26(C₅₃H₃₃NO = 699.85) 5-23 m/z = 775.29(C₅₉H₃₇NO = 775.95) 5-24 m/z = 775.29(C₅₉H₃₇NO = 775.95) 5-25 m/z = 865.30(C₆₅H₃₉NO₂ = 866.03) 5-26 m/z = 583.23(C₄₅H₂₉N = 583.73) 5-27 m/z = 685.28(C₅₃H₃₅N = 685.87) 5-28 m/z = 649.28(C₅₀H₃₅N = 649.84) 5-29 m/Z = 699.29(C₅₄H₃₇N = 699.90) 5-30 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-31 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-32 m/z = 775.32(C₆₀H₄₁N = 776.00) 5-33 m/z = 775.32(C₆₀H₄₁N = 776.00) 5-34 m/z = 775.32(C₆₀H₄₁N = 776.00) 5-35 m/z = 699.29(C₅₄H₃₇N = 699.90) 5-36 m/z = 773.31(C₆₀H₃₉N = 773.98) 5-37 m/z = 715.23(C₅₃H₃₃NS = 715.91) 5-38 m/z = 739.29(C₅₆H₃₇NO = 739.92) 5-39 m/z = 699.26(C₅₃H₃₃NO = 699.85) 5-40 m/z = 662.25(C₄₈H₃₀N₄ = 662.80) 5-41 m/z = 685.28(C₅₃H₃₅N = 685.87) 5-42 m/z = 685.28(C₅₃H₃₅N = 685.87) 5-43 m/z 633.25(C₄₉H₃₁N = 633.79) 5-44 m/z = 649.28(C₅₀H₃₅N = 649.84) 5-45 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-46 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-47 m/z = 801.34(C₆₂H₄₃N = 802.03) 5-48 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-49 m/z = 849.34(C₆₆H₄₃N = 850.08) 5-50 m/z = 850.33(C₆₅H₄₂N₂ = 851.07) 5-51 m/z = 689.22(C₅₁H₃₁NS = 689.88) 5-52 m/z = 623.22(C₄₇H₂₉NO = 623.76) 5-53 m/z = 775.29(C₅₉H₃₇NO = 775.95) 5-54 m/z = 699.26(C₅₃H₃₃NO = 699.85) 5-55 m/z = 715.23(C₅₃H₃₃NS = 715.91) 5-56 m/z = 690.31(C₅₃H₃₀D₅N = 690.90) 5-57 m/z = 787.32(C₆₁H₄₁N = 788.01) 5-58 m/z = 699.29(C₅₄H₃₇N = 699.90) 5-59 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-60 m/z = 715.23(C₅₃H₃₃NS = 715.91) 5-61 m/z = 633.25(C₄₉H₃₁N = 633.79) 5-62 m/z = 583.23(C₄₅H₂₉N = 583.73) 5-63 m/z = 865.33(C₆₆H₄₃NO = 866.08) 5-64 m/z = 821.31(C₆₄H₃₉N = 822.02) 5-65 m/z = 698.27(C₅₃H₃₄N₂ = 698.87) 5-66 m/z = 659.26(C₅₁H₃₃N = 659.83) 5-67 m/z = 649.28(C₅₀H₃₅N = 649.84) 5-68 m/z = 849.34(C₆₆H₄₃N = 850.08) 5-69 m/z = 850.33(C₆₅H₄₂N₂ = 851.07) 5-70 m/z = 825.30(C₆₃H₃₉NO = 826.01) 5-71 m/z = 583.23(C₄₅H₂₉N = 583.73) 5-72 m/z = 685.28(C₅₃H₃₅N = 685.87) 5-73 m/z = 693.32(C₅₃H₂₃D₁₀N = 693.92) 5-74 m/z = 699.29(C₅₄H₃₇N = 699.90) 5-75 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-76 m/z = 775.32(C₆₀H₄₁N = 776.00) 5-77 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-78 m/z = 849.34(C₆₆H₄₃N = 850.08) 5-79 m/z = 765.31(C₅₇H₃₉N₃ = 765.96) 5-80 m/z = 775.29(C₅₉H₃₇NO = 775.95) 5-81 m/z = 685.28(C₅₃H₃₅N = 685.87) 5-82 m/z = 609.25(C₄₇H₃₁N = 609.77) 5-83 m/z = 785.31(C₆₁H₃₉N = 785.99) 5-84 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-85 m/z = 729.21(C₅₃H₃₁NOS = 729.90) 5-86 m/z = 583.23(C₄₅H₂₉N = 583.73) 5-87 m/z = 685.28(C₅₃H₃₅N = 685.87) 5-88 m/z = 735.29 (C57H37N =) 5-89 m/z = 685.28(C₅₃H₃₅N = 685.87) 5-90 m/z = 685.28(C₅₃H₃₅N = 685.87) 5-91 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-92 m/z = 749.31(C₅₈H₃₉N = 749.96) 5-93 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-94 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-95 m/z = 725.31(C₅₆H₃₉N = 725.94) 5-96 m/z = 773.31(C₆₀H₃₉N = 773.98) 5-97 m/z = 850.33(C₆₅H₄₂N₂ = 851.07) 5-98 m/z = 699.26(C₅₃H₃₃NO = 699.85) 5-99 m/z = 715.23(C₅₃H₃₃NS = 715.91)  5-100 m/z = 739.29(C₅₆H₃₇NO = 739.92)  5-101 m/z = 709.28(C₅₅H₃₅N = 709.89)  5-102 m/z = 749.31(C₅₈H₃₉N = 749.96)  5-103 m/z = 901.37(C₇₀H₄₇N = 902.15)  5-104 m/z = 660.26(C₅₀H₃₂N₂ = 660.82)  5-105 m/z = 673.24(C₅₁H₃₁NO = 673.82)  5-106 m/z = 685.28(C₅₃H₃₅N = 685.87)  5-107 m/z = 775.32(C₆₀H₄₁N = 776.00)  5-108 m/z = 772.29(C59H36N2 = 772.95)  5-109 m/z = 928.38(C₇₁H₄₈N₂ = 929.18)  5-110 m/z = 941.31(C₇₁H₄₃NS = 942.19)  5-111 m/z = 836.32(C₆₄H₄₀N₂ = 837.04)  5-112 m/z = 913.35(C₆₉H₄₃N₃ = 914.12)  5-113 m/z = 800.28(C₆₀H₃₆N₂O = 800.96)  5-114 m/z = 841.28(C₆₃H₃₉NS = 842.07)  5-115 m/z = 877.37(C₆₈H₄₇N = 878.13) 6-1  m/z = 713.31(C₅₅H₃₉N = 713.92) 6-2  m/z = 589.28(C₄₅H₃₅N = 589.78) 6-3  m/z = 639.29(C₄₉H₃₇N = 639.84) 6-4  m/z = 613.28(C₄₇H₃₅N = 613.8) 6-5  m/z = 601.28(C₄₆H₃₅N = 601.79) 6-6  m/z = 677.31 (C₅₂H₃₉N = 677.89) 6-7  m/z = 777.3(C₅₉H₃₉NO = 777.97) 6-8  m/z = 651.26(C₄₉H₃₃NO = 651.81) 6-9  m/z = 577.24(C₄₃H₃₁NO = 577.73) 6-10 m/z = 593.22(C₄₃H₃₁NS = 593.79) 6-11 m/z = 577.24(C₄₃H₃₁NO = 577.73) 6-12 m/z = 627.26(C₄₇H₃₃NO = 627.79) 6-13 m/z = 679.32(C₅₂H₄₁N = 679.91) 6-14 m/z = 651.29(C₅₀H₃₇N = 651.85) 6-15 m/z = 725.31(C₅₆H₃₉N = 725.94) 6-16 m/z = 725.31(C₅₆H₃₉N = 725.94) 6-17 m/z = 677.31(C₅₂H₃₉N = 677.89) 6-18 m/z = 601.28(C₄₆H₃₅N = 601.79) 6-19 m/z = 691.29(C₅₂H₃₇NO = 691.87) 6-20 m/z = 691.29(C₅₂H₃₇NO = 691.87) 6-21 m/z = 691.29(C₅₂H₃₇NO = 691.87) 6-22 m/z = 689.27(C₅₂H₃₅NO = 689.86) 6-23 m/z = 767.32(C₅₈H₄₁NO = 767.97) 6-24 m/z = 767.32(C₅₈H₄₁NO = 767.97) 6-25 m/z = 767.32(C₅₈H₄₁NO = 767.97) 6-26 m/z = 765.3(C₅₈H₃₉NO = 765.96) 6-27 m/z = 677.31(C₅₂H₃₉N = 677.89) 6-28 m/z = 753.34(C₅₈H₄₃N = 753.99) 6-29 m/z = 753.34(C₅₈H₄₃N = 753.99) 6-30 m/z = 819.33(C₆₁H₄₅NSi = 820.12) 6-31 m/z = 824.36(C₆₁H₄₀D₅NSi = 825.15) 6-32 m/z = 725.31(C₅₆H39N = 725.94) 6-33 m/z = 727.32(C₅₆H41N = 727.95) 6-34 m/z = 751.32(C₅₈H41N = 751 97) 34 m/z = 751.32(C₅₈H41N = 751.97) 7-1  m/z = 760.29(C₅₅H₄₀N₂S = 761) 7-2  m/z = 744.31 (C₅₅H₄₀N₂O = 744.94) 7-3  m/z = 680.32(C₅₁H₄₀N₂ = 680.9) 7-4  m/z = 720.35(C₅₄H₄₄N₂ = 720.96) 7-5  m/z = 528.26(C₃₉H₃₂N₂ = 528.7) 7-6  m/z = 578.27(C₄₃H₃₄N₂ = 578.76) 7-7  m/z = 680.32(C₅₁H₄₀N₂ = 680.9) 7-8  m/z = 634.24(C₄₅H₃₄N₂S = 634.84) 7-9  m/z = 618.27(C₄₅H₃₄N₂O = 618.78) 7-10 m/z = 634.24(C₄₅H₃₄N₂S = 634.84) 7-11 m/z = 618.27(C₄₅H₃₄N₂O = 618.78) 7-12 m/z = 652.29(C₄₉H₃₆N₂ = 652.84) 7-13 m/z = 720.35(C₅₄H₄₄N₂ = 720.96) 7-14 m/z = 760.38(C₅₇H₄₈N₂ = 761.03) 7-15 m/z = 693.31(C₅₁H₃₉N₃ = 693.89) 7-16 m/z = 584.32(C₄₃H₄₀N₂ = 584.81) 7-17 m/z = 752.32(C₅₇H₄₀N₂ = 752.96) 7-18 m/z = 742.33(C₅₆H₄₂N₂ = 742.97) 7-19 m/z = 758.28(C₅₅H₃₈N₂S = 758.98) 7-20 m/z = 768.35(C₅₈H₄₄N₂ = 769) 7-21 m/z = 650.27(C₄₉H₃₄N₂ = 650.83) 7-22 m/z = 766.33(C₅₈H₄₂N₂ = 766.99) 7-23 m/z = 750.3(C₅₇H₃₈N₂ = 750.95) 7-24 m/z = 646.24(C₄₉H₃₀N₂ = 646.79) 7-25 m/z = 817.35(C₆₁H₄₃N₃ = 818.04) 7-26 m/z = 756.26(C₅₅H₃₆N₂S = 756.97) 7-27 m/z = 830.29(C₅₁H₃₈N₂O₂ = 830.99) 7-28 m/z = 815.33(C₆₁H₄₁N₃ = 816.02) 7-29 m/z = 694.33(C₅₂H₄₂N₂ = 694.92) 7-30 m/z = 668.28(C₄₉H₃₆N₂O = 668.84) 7-31 m/z = 710.28(C₅₁H₃₈N₂S = 710.94) 7-32 m/z = 684.26(C₄₉H₃₆N₂S = 684.9) 7-33 m/z = 668.28(C₄₉H₃₆N₂O = 668.84) 7-34 m/z = 604.29(C₄₅H₃₆N₂ = 604.8) 7-35 m/z = 630.3(C₄₇H₃₈N₂ = 630.84) 7-36 m/z = 708.29(C₅₂H₃₇FN₂ = 708.88) 7-37 m/z = 830.37(C₆₃H₄₆N = 831.08) 7-38 m/z = 808.29(C₅₉H₄₀N₂S = 809.04) 7-39 m/z = 844.38(C₆₄H₄₈N₂ = 845.1) 7-40 m/z = 834.31(C₅₁H₄₂N₂S = 835.08) 7-41 m/z = 742.3(C₅₅H₃₈N₂O = 742.92) 7-42 m/z = 968.41(C₇₄H₅₂N₂ = 969.24) 7-43 m/z = 690.3(C₅₂H₃₈N₂ = 690.89) 7-44 m/z = 802.33(C₆₁H₄₂N₂ = 803.02) 7-45 m/z = 816.31(C₆₁H₄₀N₂O = 817) 7-46 m/z = 708.26(C₅₁H₃₆N₂S = 708.92) 7-47 m/z = 832.29(C₆₁H₄₀N₂S = 833.07) 7-48 m/z = 694.3(C₅₁H₃₈N₂O = 694.88) 7-49 m/z = 818.37(C₆₂H₄₆N₂ = 819.06) 7-50 m/z = 802.33(C₆₁H₄₂N₂ = 803.02) 7-51 m/z = 769.35(C₅₇H₄₃N₃ = 769.99) 8-1  m/z = 385.15(C₂₈H₁₉NO = 385.47) 8-2  m/z = 553.19(C₄₀H₂₇NS = 553.72) 8-3  m/z = 511.23(C₃₉H₂₉N = 511.67) 8-4  m/z = 501.21 (C₃₇H₂₇NO = 501.63) 8-5  m/z = 583.14(C₄₀H₂₅NS₂ = 583.77) 8-6  m/z = 511.23(C₃₉H₂₉N = 511.67) 8-7  m/z = 501.21(C₃₇H₂₇NO = 501.63) 8-8  m/z = 501.16(C₃₆H₂₃NS = 501.65) 8-9  m/z = 593.22(C₄₃H₃₁NS = 593.79) 8-10 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-11 m/z = 661.28(C₅₁H₃₅N = 661.85) 8-12 m/z = 613.24(C₄₆H₃₁NO = 613.76) 8-13 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-14 m/z = 669.25(C₄₉H₃₅NS = 669.89) 8-15 m/z = 777.30(C₅₉H₃₉NO = 777.97) 8-16 m/z = 643.20(C₄₆H₂₉NOS = 643.8) 8-17 m/z = 774.30(C₅₉H₃₈N₂ = 774.97) 8-18 m/z = 702.27(C₅₂H₃₄N₂O = 702.86) 8-19 m/z = 593.21(C₄₀H₁₅D₁₀NS₂ = 593.83) 8-20 m/z = 841.37(C₆₅H₄₇N = 842.10) 8-21 m/z = 461.18(C₃₄H₂₃NO = 461.56) 8-22 m/z = 491.13(C₃₄H₂₁NOS = 491.61) 8-23 m/z = 511.23(C₃₉H₂₉N = 511.67) 8-24 m/z = 553.19(C₄₀H₂₇NS = 553.72) 8-25 m/z = 725.31(C₅₆H₃₉N = 725.94) 8-26 m/z = 541.15(C₃₈H₂₃NOS = 541.67) 8-27 m/z = 583.14(C₄₀H₂₅NS₂ = 583.77) 8-28 m/z = 557.24(C₄₃H₃₁NO = 557.73) 8-29 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-30 m/z = 727.32(C₅₆H₄₁N = 727.95) 8-31 m/z = 627.22(C₄₆H₂₉NO₂ = 627.74) 8-32 m/z = 593.22(C₄₃H₃₁NS = 593.79) 8-33 m/z = 723.39(C₅₅H₄₉N = 724.00) 8-34 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-35 m/z = 643.23(C₄₇H₃₃NS = 643.85) 8-36 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-37 m/z = 583.14(C₄₀H₂₅NS₂ = 583.77) 8-38 m/z = 563.26(C₄₃H₃₃N = 563.74) 8-39 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-40 m/z = 629.22(C₄₆H₃₁NS = 629.82) 8-41 m/z = 537.21(C₄₀H₂₇NO = 537.66) 8-42 m/z = 437.10(C₂₈H₁₇F₂NS = 437.51) 8-43 m/z = 461.19(C₃₃H₂₃N₃ = 461.57) 8-44 m/z = 551.19(C₄₀H₂₅NO₂ = 551.65) 8-45 m/z = 567.20(C₄₁H₂₉NS = 567.75) 8-46 m/z = 593.22(C₄₃H₃₁NS = 593.79) 8-47 m/z = 601.20(C₄₄H₂₇NO₂ = 601.71) 8-48 m/z = 659.17(C₄₆H₂₉NS₂ = 659.87) 8-49 m/z = 749.27(C₅₇H₃₅NO = 749.91) 8-50 m/z = 643.20(C₄₆H₂₉NOS = 643.80) 8-51 m/z = 537.21(C₄₀H₂₇NO = 537.66) 8-52 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-53 m/z = 577.28(C₄₄H₃₅N = 577.77) 8-54 m/z = 623.23(C₄₄H₃₃NOS = 623.81) 8-55 m/z = 582.12(C₃₉H₂₂N₂S₂ = 582.74) 8-56 m/z = 793.28(C₅₈H₃₉NS = 794.03) 8-57 m/z = 561.21(C₄₂H₂₇NO = 561.68) 8-58 m/z = 669.25(C₄₉H₃₅NS = 669.89) 8-59 m/z = 715.23(C₅₃H₃₃NS = 715.91) 8-60 m/z = 643.20(C₅₃H₃₃NS = 643.80) 8-61 m/z = 669.25(C₄₉H₃₅NS = 669.89) 8-62 m/z = 759.26(C₅₅H₃₇NOS = 759.97) 8-63 m/z = 643.20(C₄₆H₂₉NOS = 643.80) 8-64 m/z = 659.17(C₄₆H₂₉NS₂ = 659.87) 8-65 m/z = 807.26(C₅₉H₃₇NOS = 808.01) 8-66 m/z = 501.21(C₃₇H₂₇NO = 501.63) 8-67 m/z = 553.19(C₄₀H₂₇NS = 553.72) 8-68 m/z = 593.22(C₄₃H₃₁NS = 593.79) 8-69 m/z = 485.18(C₃₆H₂₃NO = 485.59) 8-70 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-71 m/z = 809.31(C₆₀H₄₃NS = 810.07) 8-72 m/z = 593.27(C₄₄H₃₅NO = 593.77) 8-73 m/z = 583.14(C₄₀H₂₅NS₂ = 583.77) 8-74 m/z = 593.27(C₄₄H₃₅NO = 593.77) 8-75 m/z = 659.23(C₄₇H₃₃NOS = 659.85) 8-76 m/z = 759.26(C₅₅H₃₇NOS = 759.97) 8-77 m/z = 593.22(C₄₃H₃₁NS = 593.79) 8-78 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-79 m/z = 667.20(C₄₈H₂₉NOS = 667.83) 8-80 m/z = 698.27(C₅₃H₃₄N₂ = 698.87) 8-81 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-82 m/z = 501.16(C₃₆H₂₃NS = 501.65) 8-83 m/z = 593.22(C₄₃H₃₁NS = 593.79) 8-84 m/z = 537.21(C₄₀H₂₇NO = 537.66) 8-85 m/z = 553.19(C₄₀H₂₇NS = 553.72) 8-86 m/z = 593.22(C₄₃H₃₁NS = 593.79) 8-87 m/z = 537.21(C₄₀H₂₇NO = 537.66) 8-88 m/z = 642.21 (C₄₆H₃₀N₂S = 642.82) 8-89 m/z = 725.31(C₅₆H₃₉N = 725.94) 8-90 m/z = 551.19(C₄₀H₂₅NO₂ = 551.65) 8-91 m/z = 567.17(C₄₀H₂₅NOS = 567.71) 8-92 m/z = 593.22(C₄₃H₃₁NS = 593.79) 8-93 m/z = 577.24(C₄₃H₃₁NO = 577.73) 8-94 m/z = 583.14(C₄₀H₂₅NS₂ = 583.77) 8-95 m/z = 701.27(C₅₃H₃₅NO = 701.87) 8-96 m/z = 525.17(C₃₈H₂₃NO₂ = 525.61) 8-97 m/z = 527.17(C₃₈H₂₅NS = 527.69) 8-98 m/z = 567.20(C₄₁H₂₉NS = 567.75) 8-99 m/z = 541.15(C₃₈H₂₃NOS = 541.67)  8-100 m/z = 527.17(C₃₈H₂₅NS = 527.69)  8-101 m/z = 583.23(C₄₅H₂₉N = 583.73)  8-102 m/z = 551.22(C₄₁H₂₉NO = 551.69)  8-103 m/z = 603.20(C₄₄H₂₉NS = 603.78)  8-104 m/z = 585.25(C₄₅H₃₁N = 585.75) 10-1  m/z = 618.21(C₄₄H₃₀N₂S = 618.80) 10-2  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-3  m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 10-4  m/z = 692.25(C₅₀H₃₂N₂O₂ = 692.82) 10-5  m/z = 742.30(C₅₅H₃₈N₂O = 742.92) 10-6  m/z = 654.27(C₄₈H₃₄N₂O = 654.81) 10-7  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-8  m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) 10-9  m/z = 730.16(C₄₈H₃₀N₂S₃ = 730.96) 10-10  m/z = 734.24(C₅₂H₃₄N₂OS = 734.92) 10-11  m/z = 872.32(C₆₄H₄₄N₂S = 873.13) 10-12  m/z = 718.26(C₅₂H₃₄N₂O₂ = 718.86) 10-13  m/z = 568.20(C₄₀H₂₈N₂S = 568.74) 10-14  m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 10-15  m/z = 658.21(C₄₆H₃₀N₂OS = 658.82) 10-16  m/z = 730.30(C₅₄H₃₈N₂O = 730.91) 10-17  m/z = 698.20(C₄₈H₃₀N₂O₂S = 698.84) 10-18  m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 10-19  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-20  m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 10-21  m/z = 750.22(C₅₂H₃₄N₂S₂ = 750.98) 10-22  m/z = 776.23(C₅₄H₃₆N₂S₂ = 777.02) 10-23  m/z = 867.24(C₅₉H₃₇N₃OS₂ = 868.09) 10-24  m/z = 759.27(C₅₄H₃₇N₃S = 759.97) 10-25  m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 10-26  m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 10-27  m/z = 692.25(C₅₀H₃₂N₂O₂ = 692.82) 10-28  m/z = 894.20(C₆₀H₃₄N₂O₃S₂ = 895.06) 10-29  m/z = 618.21(C₄₄H₃₀N₂S = 618.80) 10-30  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-31  m/z = 780.17(C₅₂H₃₂N₂S₃ = 781.02) 10-32  m/z = 734.24(C₅₂H₃₄N₂OS = 734.92) 10-33  m/z = 834.31(C₆₁H₄₂N₂S = 835.08) 10-34  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-35  m/z = 724.25(C₅₁H₃₆N₂OS = 724.92) 10-36  m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 10-37  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-38  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-39  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-40  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-41  m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 10-42  m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-43  m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-44  m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 10-45  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-46  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-47  m/z = 826.25(C₅₈H₃₈N₂S₂ = 827.08) 10-48  m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 10-49  m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 10-50  m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-51  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-52  m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-53  m/z = 730.16(C₄₈H₃₀N₂S₃ = 730.96) 10-54  m/z = 826.25(C₅₈H₃₈N₂S₂ = 827.08) 10-55  m/z = 806.19(C₅₄H₃₄N₂S₃ = 807.06) 10-56  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-57  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-58  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-59  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-60  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-61  m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 10-62  m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 10-63  m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 10-64  m/z = 622.21(C₄₃H₃₀N₂OS = 622.79) 10-65  m/z = 688.20(C₄₇H₃₂N₂S₂ = 688.91) 10-66  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-67  m/z = 789.23(C₅₄H₃₅N₃S₂ = 790.02) 10-68  m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 10-69  m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 10-70  m/z = 642.16(C₄₂H₂₇FN₂S₂ = 642.81) 10-71  m/z = 638.19(C₄₃H₃₀N₂S₂ = 638.85) 10-72  m/z = 714.22(C₄₉H₃₄N₂S₂ = 714.95) 10-73  m/z = 716.20(C₄₈H₃₂N₂OS₂ = 716.92) 10-74  m/z = 670.24(C₄₈H₃₄N₂S = 670.87) 10-75  m/z = 634.24(C₄₅H₃₄N₂S = 634.84) 10-76  m/z = 759.27(C₅₄H₃₇N₃S = 759.97) 10-77  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-78  m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 10-79  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-80  m/z = 748.22(C₅₂H₃₂N₂O₂S = 748.90) 10-81  m/z = 821.29(C₅₇H₃₅D₅N₂S₂ = 822.11) 10-82  m/z = 730.16(C₄₈H₃₀N₂S₃ = 730.96) 10-83  m/z = 730.16(C₄₈H₃₀N₂S₃ = 730.96) 10-84  m/z = 714.18(C₄₈H₃₀N₂OS₂ = 714.90) 10-85  m/z = 882.22(C₆₀H₃₈N₂S₃ = 883.16) 10-86  m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 10-87  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-88  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-89  m/z = 674.19(C₄₅H₃₀N₂S₂ = 674.88) 10-90  m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 10-91  m/z = 759.27(C₅₄H₃₇N₃S = 759.97) 10-92  m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-93  m/z = 688.20(C₄₇H₃₂N₂S₂ = 688.91) 10-94  m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) 10-95  m/z = 759.27(C₅₄H₃₇N₃S = 759.97) 10-96  m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 10-97  m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-98  m/z = 622.21(C₄₃H₃₀N₂OS = 622.79) 10-99  m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) 10-100 m/z = 658.21(C₄₆H₃₀N₂OS = 658.82) 10-101 m/z = 658.21(C₄₆H₃₀N₂OS = 658.82) 10-102 m/z = 692.25(C₅₀H₃₂N₂O₂ = 692.82) 10-103 m/z = 628.25(C₄₆H₃₂N₂O = 628.78) 10-104 m/z = 693.28(C₅₀H₃₅N₃O = 693.85) 10-105 m/z = 723.23(C₅₀H₃₃N₃OS = 723.89) 10-106 m/z = 749.29(C₅₄H₃₁D₅N₂S = 749.99) 10-107 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-108 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-109 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-110 m/z = 724.25(C₅₁H₃₆N₂OS = 724.92) 10-111 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-112 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-113 m/z = 780.17(C₅₂H₃₂N₂S₃ = 781.02) 10-114 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-115 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-116 m/z = 698.20(C₄₈H₃₀N₂O₂S = 698.84) 10-117 m/z = 618.26(C₄₂H₁₈D₁₀N₂OS = 618.82) 10-118 m/z = 757.27(C₅₄H₃₅N₃O₂ = 757.89) 10-119 m/z = 668.25(C₄₈H₃₂N₂O₂ = 668.80) 10-120 m/z = 720.26(C₅₂H₃₆N₂S = 720.93) 10-121 m/z = 670.24(C₄₈H₃₄N₂S = 670.87) 10-122 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-123 m/z = 674.19(C₄₆H₃₀N₂S = 674.88) 10-124 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-125 m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 10-126 m/z = 860.25(C₅₈H₄₀N₂O₂S₂ = 861.09) 10-127 m/z = 798.27(C₅₇H₃₈N₂OS = 799.00) 10-128 m/z = 734.33(C₅₄H₄₂N₂O = 734.94) 10-129 m/z = 742.26(C₅₄H₃₄N₂O₂ = 742.88) 10-130 m/z = 945.37(C₇₀H₄₇N₃O = 946.17) 10-131 m/z = 670.24(C₄₈H₃₄N₂S = 670.87) 10-132 m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 10-133 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-134 m/z = 724.20(C₅₀H₃₂N₂S₂ = 724.94) 10-135 m/z = 816.26(C₅₇H₄₀N₂S₂ = 817.08) 10-136 m/z = 760.25(C₅₄H₃₅N₂OS = 760.96) 10-137 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-138 m/z = 730.16(C₄₈H₃₀N₂S₃ = 730.96) 10-139 m/z = 881.29(C₆₁H₄₃N₃S₂ = 882.16) 10-140 m/z = 704.28(C₅₂H₃₆N₂O = 704.87) 10-141 m/z = 608.19(C₄₂H₂₈N₂OS = 608.76) 10-142 m/z = 682.23(C₄₈H₃₀N₂O₃ = 682.78) 10-143 m/z = 670.24(C₄₈H₃₄N₂S = 670.87) 10-144 m/z = 776.23(C₅₄H₃₆N₂S₂ = 777.02) 10-145 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-146 m/z = 759.27(C₅₄H₃₇N₃S = 759.97) 10-147 m/z = 758.24(C₅₄H₃₄N₂OS = 758.94) 10-148 m/z = 806.28(C₅₉H₃₈N₂S = 807.03) 10-149 m/z = 823.30(C₅₉H₃₈FN₃O = 823.97) 10-150 m/z = 743.29(C₅₄H₃₇N₃O = 743.91) 10-151 m/z = 998.33(C₇₃H₄₆N₂OS = 999.24) 10-152 m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.92) 10-153 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-154 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-155 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-156 m/z = 674.19(C₄₆H₃₀N₂S₂ = 674.88) 10-157 m/z = 762.29(C₅₀H₄₆N₂SSi₂ = 763.16) 10-158 m/z = 624.17(C₄₂H₂₈N₂S₂ = 624.82) 10-159 m/z = 784.25(C₅₆H₃₆N₂OS = 784.98) 10-160 m/z = 810.27(C₅₈H₃₈N₂OS = 811.02) 10-161 m/z = 860.29(C₆₂H₄₀N₂OS = 861.08) 10-162 m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 10-163 m/z = 742.26(C₅₄H₃₄N₂O₂ = 742.88) 10-164 m/z = 828.26(C₅₈H₄₀N₂S₂ = 829.09) 10-165 m/z = 708.22(C₅₀H₃₂N₂OS = 708.88) 10-166 m/z = 724.20(C₅₀H₃₂N₂S₂ = 724.94) 10-167 m/z = 834.27(C₆₀H₃₈N₂OS = 835.04) 10-168 m/z = 768.28(C₅₆H₃₆N₂O₂ = 768.92) 10-169 m/z = 830.19(C₅₆H₃₄N₂S₃ = 831.08) 10-170 m/z = 810.27(C₅₈H₃₈N₂OS = 811.02) 10-171 m/z = 810.31(C₅₉H₄₂N₂S = 811.06) 10-172 m/z = 692.25(C₅₀H₃₂N₂O₂ = 692.82) 10-173 m/z = 758.24(C₅₄H₃₄N₂OS = 758.94) 10-174 m/z = 783.27(C₅₆H₃₇N₃S = 783.99) 10-175 m/z = 808.25(C₅₈H₃₆N₂OS = 809.00) 10-176 m/z = 806.19(C₅₄H₃₄N₂S₃ = 807.06) 10-177 m/z = 764.2(C₅₂H₃₂N₂OS₂ = 764.96) 10-178 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-179 m/z = 774.27(C₅₅H₃₈N₂OS = 774.98) 10-180 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-181 m/z = 658.21(C₄₆H₃₀N₂OS = 658.82) 10-182 m/z = 700.2(C₄₈H₃₂N₂S₂ = 700.92) 10-183 m/z = 700.2(C₄₈H₃₂N₂S₂ = 700.92) 10-184 m/z = 700.2(C₄₈H₃₂N₂S₂ = 700.92) 10-185 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-186 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) 10-187 m/z = 724.25(C₅₁H₃₆N₂OS = 724.92) 10-188 m/z = 832.31(C₅₁H₄₀N₂O₂ = 833) 10-189 m/z = 861.37(C₆₃H₄₇N₃O = 862.09) 11-1  m/z = 473.21(C₃₆H₂₇N = 473.61) 11-2  m/z = 523.23(C₄₀H₂₉N = 523.66) 11-3  m/z = 573.25(C₄₄H₃₁N = 573.72) 11-4  m/z = 623.26(C₄₈H₃₃N = 623.78) 11-5  m/z = 447.20(C₃₄H₂₅N = 447.57) 11-6  m/z = 371.17(C₂₈H₂₁N = 371.47) 11-7  m/z = 471.20(C₃₆H₂₅N = 471.59) 11-8  m/z = 521.21(C₄₀H₂₇N = 521.65) 11-9  m/z = 549.25(C₄₂H₃₁N = 549.70) 11-10  m/z = 625.28(C₄₈H₃₅N = 625.80) 11-11  m/z = 675.29(C₅₂H₃₇N = 675.86) 11-12  m/z = 473.21(C₃₆H₂₇N = 473.61) 11-13  m/z = 523.23(C₄₀H₂₉N = 523.66) 11-14  m/z = 623.26(C₄₈H₃₃N = 623.78) 11-15  m/z = 549.25(C₄₂H₃₁N = 549.70) 11-16  m/z = 625.28(C₄₈H₃₅N = 625.80) 11-17  m/z = 473.21(C₃₆H₂₇N = 473.62) 11-18  m/z = 725.31(C₅₆H₃₉N = 725.94) 11-19  m/z = 625.28(C₄₈H₃₅N = 625.82) 11-20  m/z = 749.31(C₅₈H₃₉N = 749.96) 11-21  m/z = 699.29(C_(M4)H₃₇N = 699.9) 11-22  m/z = 730.34(C₅₆H₃₄D₅N = 730.97) 11-23  m/z = 753.33(C₅₈H₃₅D₄N = 753.98) 12-1  m/z = 690.30(C₅₂H₃₈N₂ = 690.87) 12-2  m/z = 790.33(C₆₀H₄₂N₂ = 790.99) 12-3  m/z = 740.32(C₅₆H₄₀N₂ = 740.93) 12-4  m/z = 840.35(C₆₄H₄₄N₂ = 841.05) 12-5  m/z = 691.30(C₅₁H₃₇N₃ = 691.86) 12-6  m/z = 688.29(C₅₂H₃₆N₂ = 688.86) 12-7  m/z = 700.37(C₅₂H₂₈D₁₀N₂ = 700.93) 12-8  m/z = 650.35(C₄₈H₂₆D₁₀N₂ = 650.87) 12-9  m/z = 922.40(C₆₈H₅₀N₄ = 923.15) 12-10  m/z = 730.33(C₅₅H₄₂N₂ = 730.94) 12-11  m/z = 832.38(C₆₃H₄₈N₂ = 833.07) 12-12  m/z = 761.38(C₅₇H₃₉D₅N₂ = 762.00) 12-13  m/z = 806.37(C₆₁H₄₅N₂ = 807.03) 12-14  m/z = 876.35(C₆₄H₄₈N₂S = 877.14) 12-15  m/z = 872.41(C₆₆H₅₂N₂ = 873.13) 12-16  m/z = 770.37(C₅₈H₄₆N₂ = 771.00) 12-17  m/z = 952.48(C₇₂H₆₀N₂ = 953.26) 12-18  m/z = 828.35(C₆₃H₄₄N₂ = 829.04) 12-19  m/z = 910.34(C₆₇H₄₆N₂S = 911.16) 12-20  m/z = 863.33(C₆₂H₄₅N₃S = 864.11) 12-21  m/z = 804.35(C₆₁H₄₄N₂ = 805.02) 12-22  m/z = 970.39(C₇₃H₅₀N₂O = 971.19) 12-23  m/z = 981.41(C₇₄H₅₁N₃ = 982.22) 12-24  m/z = 968.41 (C₇₄H₅₂N₂ = 969.22) 12-25  m/z = 878.37(C₆₇H₄₆N₂ = 879.10) 12-26  m/z = 816.31 (C₆₁H₄₀N₂O = 816.98) 12-27  m/z = 805.35(C₆₀H₄₃N₃ = 806.00) 12-28  m/z = 885.32(C₆₄H₄₃N₃S = 886.11) 12-29  m/z = 805.35(C₆₀H₄₃N₃ = 806.00) 12-30  m/z = 1050.47(C₇₈H₅₈N₄ = 1051.32) 12-31  m/z = 696.26(C₅₀H₃₆N₂S = 696.90) 12-32  m/z = 696.26(C₅₀H₃₆N₂S = 696.90) 12-33  m/z = 822.31(C₆₀H₄₂N₂S = 823.05) 12-34  m/z = 746.28(C₅₄H₃₈N₂S = 746.96) 12-35  m/z = 700.20(C₄₈H₃₂N₂S₂ = 700.91) 12-36  m/z = 800.23(C₅₆H₃₆N₂S₂ = 801.03) 12-37  m/z = 852.26(C₆₀H₄₀N₂S₂ = 853.10) 12-38  m/z = 952.29(C₆₈H₄₄N₂S₂ = 953.22) 12-39  m/z = 912.18(C₅₀H₃₆N₂S₄ = 913.20) 12-40  m/z = 852.26(C₆₀H₄₀N₂S₂ = 853.10) 12-41  m/z = 806.33(C₆₀H₄₂N₂O = 806.99) 12-42  m/z = 768.28(C₅₆H₃₆N₂O₂ = 768.90) 12-43  m/z = 920.34(C₆₃H₄₄N₂O₂ = 921.09) 12-44  m/z = 684.22(C₄₈H₃₂N₂OS = 684.85) 12-45  m/z = 970.43(C₇₄H₅₄N₂ = 971.23) 12-46  m/z = 947.42(C₇₁H₅₃N₃ = 948.20) 12-47  m/z = 829.35(C₆₂H₄₃N₃ = 830.02) 12-48  m/z = 860.29(C₆₂H₄₀N₂OS = 861.06) 12-49  m/z = 664.29(C₅₀H₃₆N₂ = 664.83) 12-50  m/z = 956.41(C₇₃H₅₂N₂ = 957.21) 12-51  m/z = 829.35(C₆₂H₄₃N₃ = 830.02) 12-52  m/z = 911.33(C₆₅H₄₅N₃S = 912.15) 12-53  m/z = 664.29(C₅₀H₃₆N₂ = 664.83) 12-54  m/z = 776.23(C₅₄H₃₆N₂S₂ = 777.01) 12-55  m/z = 744.28(C₅₄H₃₆N₂O₂ = 744.88) 12-56  m/z = 894.37(C₆₆H₄₆N₄ = 895.10) 12-57  m/z = 776.23(C₅₄H₃₆N₂S₂ = 777.01) 12-58  m/z = 844.31 (C₆₂H₄₀N₂O₂ = 844.99) 12-59  m/z = 664.29(C₅₀H₃₆N₂ = 664.83) 12-60  m/z = 844.31 (C₆₂H₄₀N₂O₂ = 844.99) 12-61  m/z = 640.29(C₄₈H₃₆N₂ = 640.83) 12-62  m/z = 604.29(C₄₅H₃₆N₂ = 604.8) 12-63  m/z = 578.24(C₄₂H₃₀N₂O = 578.72) 12-64  m/z = 654.27(C₄₈H₃₄N₂O = 654.81) 12-66  m/z = 730.3(C₅₄H₃₈N₂O = 730.91) 12-68  m/z = 770.33(C₅₇H₄₂N₂O = 770.93) 12-70  m/z = 668.25(C₄₈H₃₂N₂O₂ = 668.8) 12-71  m/z = 952.48(C₇₂H₆₀N₂ = 953.26)

[Synthesis Example 2] Synthesis Example of Formula 2

Compound (final product 2) represented by Formula 2 according to the present invention may be synthesized as shown in Reaction Scheme 7 below, but there is not limited thereto.

Synthesis of Sub3

Sub3 of Reaction Scheme 7 may be synthesized by the reaction route of Reaction Scheme 8, but there is not limited thereto. Sub3 can be synthesized according to the synthesis route of (1) when X¹ is —OH, according to the synthesis route of (2) when X¹ is —SH, and according to the synthesis route of (3) when X¹ is —NH₂.

(1) Synthesis Example Sub3-20

Synthesis of Sub3-20-a

After adding THF (100 ml) to 2-bromophenyl)(phenyl)sulfane (9.40 g, 35.45 mmol), 2.5M n-BuLi (14.18 ml, 35.45 mmol) was slowly added to the solution at −78° C. and the mixture was stirred for 1 hour. Thereafter, 2-bromo-9H-fluoren-9-one (9.18 g, 35.45 mmol) dissolved in THF (50 ml) was added to the mixture at −78° C., and then the reaction temperature was slowly raised to room temperature. When the reaction was completed, the solvent was removed after quenching with NH₄Cl. Acetic acid (100 ml) and HCl (20 ml) are added to the reaction product and the mixture was stirred at 80° C. for 5 hours. When the reaction was completed, the temperature was lowered to room temperature, the reaction product was filtered and the filtrate was extracted with MC, and washed with water. An organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column to obtain 10.45 g (69%) of the product.

Synthesis of Sub3-20

Bis(pinacolato)diboron (8.46 g, 30.19 mmol), PdCl₂(dppf)₂ (0.82 g, 1.01 mmol), KOAc (3.95 g, 40.25 mmol) and toluene (100 ml) were added to Sub3-20-a (8.60 g, 21.12 mmol) and the mixture was refluxed at 120° C. for 6 hours. When the reaction was completed, the temperature of the reaction product is cooled to room temperature, the reaction product was extracted with MC and washed with water. An organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column to obtain 7.64 g (80%) of the product.

(2) Synthesis of Sub3-5

Synthesis of Sub3-5-a

After 1-bromo-2-phenoxybenzene (11.00 g, 44.16 mmol) was dissolved in THF (150 ml), 2.5M n-BuLi (17.66 ml, 44.16 mmol), 3-bromo-9H-fluoren-9-one (11.44 g, 44.16 mmol), AcOH (110 ml) and HCl (20 ml) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of Sub3-20-a to obtain 13.08 g (72%) of the product.

Synthesis of Sub3-5

Bis(pinacolato)diboron (7.56 g, 26.99 mmol), PdCl₂(dppf)₂ (0.73 g, 0.90 mmol), KOAc (3.53 g, 35.98 mmol) and toluene (100 ml) were added to Sub-1-7-a (7.40 g, 17.99 mmol), and then the synthesis was carried out in the same manner as in the synthesis method of Sub3-20 to obtain 6.68 g (81%) of the product.

(2) Synthesis of Sub3-34

Synthesis of Sub3-34-a

After (2-bromophenyl)(phenyl)sulfane (7.0 g, 26.40 mmol) was dissolved in THF (88 ml), 2.5M n-BuLi (1.69 g, 26.40 mmol), 2,4-dibromo-9H-fluoren-9-one (8.92 g, 26.40 mmol), AcOH (61 ml) and HCl (13.2 ml) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of Sub3-20-a to obtain 8.02 g (60%) of the product.

Synthesis of Sub3-34

Bis(pinacolato)diboron (4.43 g, 17.43 mmol), PdCl₂(dppf)₂ (0.39 g, 0.48 mmol), KOAc (4.66 g, 47.52 mmol) and toluene (79 ml) were added to Sub3-34-a (8.02 g, 15.84 mmol), and then the synthesis was carried out in the same manner as in the synthesis method of Sub3-20-a to obtain 6.66 g (70%) of the product.

(3) Synthesis of Sub3-35

Synthesis of Sub3-35-a

After 2-bromo-N-(4-bromophenyl)-N-phenylaniline (8.5 g, 21.09 mmol) was dissolved in THF (70.3 ml), 2.5M n-BuLi (1.35 g, 21.09 mmol), 9H-fluoren-9-one (3.80 g, 21.09 mmol), AcOH (49.04 ml) and HCl (10.5 ml) were added to the solution, and then the synthesis was carried out in the same manner as in the synthesis method of Sub3-20-a to obtain 5.50 g (64%) of the product.

Synthesis of Sub3-35

Bis(pinacolato)diboron (3.30 g, 11.95 mmol), PdCl₂(dppf)₂ (0.27 g, 0.33 mmol), KOAc (3.20 g, 32.59 mmol), toluene (54 ml) were added to Sub3-35-a (5.50 g, 10.86 mmol), and then the synthesis was carried out in the same manner as in the synthesis method of Sub3-20 to obtain 4.44 g (68%) of the product.

Compounds belong to Sub 3 are as follows, but are not limited thereto, and FD-MS values of the compounds are shown in Table 5 below.

TABLE 5 Compound FD-MS Compound FD-MS Sub3-1 m/z = 458.21(C₃₁H₂₇BO₃ = 458.36) Sub3-2 m/z = 458.21(C₃₁H₂₇BO₃ = 458.36) Sub3-3 m/z = 458.21(C₃₁H₂₇BO₃ = 458.36) Sub3-4 m/z = 458.21(C₃₁H₂₇BO₃ = 458.36) Sub3-5 m/z = 458.21(C₃₁H₂₇BO₃ = 458.36) Sub3-6 m/z = 458.21(C_(3l)H₂₇BO₃ = 458.36) Sub3-7 m/z = 458.21(C₃₁H₂₇BO₃ = 458.36) Sub3-8 m/z = 458.21(C_(3l)H₂₇BO₃ = 458.36) Sub3-9 m/z = 584.29(C₃₇H_(3S)B₂O₅ = 584.33) Sub3-10 m/z = 584.29(C₃₇H_(3S)B₂O₅ = 584.33) Sub3-11 m/z = 584.29(C₃₇H_(3S)B₂O₅ = 584.33) Sub3-12 m/z = 584.29(C₃₇H_(3S)B₂O₅ = 584.33) Sub3-13 m/z = 508.22(C₃₅H₂₉BO₃ = 508.42) Sub3-14 m/z = 508.22(C_(3S)H₂₉BO₃ = 508.42) Sub3-15 m/z = 684.32(C₄₅H₄₂B₂O₅ = 684.45) Sub3-16 m/z = 684.32(C₄₅H₄₂B₂O₅ = 684.45) Sub3-17 m/z = 684.32(C₄₅H₄₂B₂O₅ = 684.45) Sub3-18 m/z = 584.29(C₃₇H_(3S)B₂O₅ = 584.33) Sub3-19 m/z = 474.18(C₃₁H₂₇BO₂S = 474.43) Sub3-20 m/z = 474.18(C₃₁H₂₇BO₂S = 474.43) Sub3-21 m/z = 474.18(C₃₁H₂₇BO₂S = 474.43) Sub3-22 m/z = 474.18(C₃₁H₂₇BO₂S = 474.43) Sub3-23 m/z = 600.27(C₃₇H₃₈B₂O₄S = 600.39) Sub3-24 m/z = 474.18(C₃₁H₂₇BO₂S = 474.43) Sub3-25 m/z = 524.2(C₃₅H₂₉BO₂S = 524.49) Sub3-26 m/z = 524.2(C₃₅H₂₉BO₂S = 524.49) Sub3-27 m/z = 524.2(C₃₅H₂₉BO₂S = 524.49) Sub3-28 m/z = 600.27(C₃₇H₃₈B₂O₄S = 600.39) Sub3-29 m/z = 726.35(C₄₃H₄₉B₃O₆S = 726.35) Sub3-30 m/z = 600.27(C₃₇H₃₈B₂O₄S = 600.39) Sub3-31 m/z = 600.27(C₃₇H₃₈B₂O₄S = 600.39) Sub3-32 m/z = 474.18(C₃₁H₂₇BO₂S = 474.43) Sub3-33 m/z = 474.18(C₃₁H₂₇BO₂S = 474.43) Sub3-34 m/z = 600.27(C₃₇H₃₈B₂O₄S = 600.39) Sub3-35 m/z = 533.25(C₃₇H₃₂BNO₂ = 533.48) Sub3-36 m/z = 533.25(C₃₇H₃₂BNO₂ = 533.48) Sub3-37 m/z = 533.25(C₃₇H₃₂BNO₂ = 533.48) Sub3-38 m/2 = 533.25(C₃₇H₃₂BNO₂ = 533.48) Sub3-39 m/z = 533.25(C₃₇H₃₂BNO₂ = 533.48) Sub3-40 m/z = 557.25(C₃₉H₃₂BNO₂ = 557.5) Sub3-41 m/z = 507.24(C₃₅H₃₀BNO₂ = 507.44) Sub3-42 m/z = 507.24(C₃₅H₃₀BNO₂ = 507.44) Sub3-43 m/z = 583.31(C₃₇H₃₉B₂NO₄ = 583.34) Sub3-44 m/z = 583.31(C₃₇H₃₉B₂NO₄ = 583.34) Sub3-45 m/z = 583.31(C₃₇H₃₉B₂NO₄ = 583.34) Sub3-46 m/z = 546.25(C₃₇H₃₁BN₂O₂ = 546.48) Sub3-47 m/z = 563.21(C₃₇H₃₀BNO₂S = 563.52) Sub3-48 m/z = 763.38(C₄₉H₄₇B₂N₃O₄ = 763.55) Sub3-49 m/z = 547.23(C₃₇H₃₀BNO₃ = 547.46) Sub3-50 m/z = 584.29(C₃₇H₃₈B₂O₅ = 584.33)

Synthesis Example of Sub 4

Sub 4 of Reaction Scheme 7 may be synthesized as shown in Reaction Scheme 8, but there is not limited thereto.

(1) Synthesis of Sub4-19

Sub4-19b (6.55 g, 53.32 mmol), Pd(PPh₃)₄ (2.05 g, 1.78 mmol), K₂CO₃ (18.42 g, 133.29 mmol), THF (163 ml) and H₂O (81 ml) were added to sub 4-19a (10 g, 44.43 mmol) and the mixture was refluxed at 120° C. for 3 hours. When the reaction was completed, the temperature of the reaction product was cooled to room temperature. The resulting solid was filtered and it dissolved in o-DCB. Then, the resultant was separated by a silica filter and recrystallized to obtain 8.09 g (68%) of the product.

(2) Synthesis of Sub4-34

Sub4-34b (14.22 g, 56.89 mmol), Pd(PPh₃)₄ (2.19 g, 1.90 mmol), K₂CO₃ (19.66 g, 142.21 mmol), THF (174 ml) and H₂O (87 ml) were added to Sub4-34a (12 g, 47.40 mmol), and then the synthesis was carried out in the same manner as in the synthesis method of Sub4-19 to obtain 13.03 g (65%) of the product.

(3) Synthesis of Sub4-45

Sub4-45b (13.85 g, 37.92 mmol), Pd(PPh₃)₄ (1.46 g, 1.26 mmol), K₂CO₃ (13.10 g, 94.81 mmol), THF (116 ml) and H₂O (58 ml) were added to Sub4-45a (8 g, 31.60 mmol), and then the synthesis was carried out in the same manner as in the synthesis method of Sub4-19 to obtain 10.54 g (62%) of the product.

(4) Synthesis of Sub4-70

Sub4-70b (20.87 g, 79.62 mmol), Pd(PPh₃)₄ (3.07 g, 2.65 mmol), K₂CO₃ (27.51 g, 199.06 mmol), THF (243 ml) and H₂O (122 ml) were added to Sub4-70a (15 g, 66.35 mmol), and then the synthesis was carried out in the same manner as in the synthesis method of Sub4-19 to obtain 19.49 g (72%) of the product.

(5) Synthesis of Sub4-83

Sub4-83b (13.98 g, 45.97 mmol), Pd(PPh₃)₄ (1.77 g, 1.53 mmol), K₂CO₃ (15.88 g, 114.93 mmol), THF (140 ml) and H₂O (70 ml) were added to Sub4-83a (11 g, 38.31 mmol), and then the synthesis was carried out in the same manner as in the synthesis method of Sub4-19 to obtain 14.49 g (74%) of the product.

(6) Synthesis of Sub4-105

Sub4-105b (44.99 g, 146.94 mmol), Pd(PPh₃)₄ (5.66 g, 4.9 mmol), K₂CO₃ (50.77 g, 367.35 mmol), THF (449 ml) and H₂O (224 ml) were added to Sub4-105a (18 g, 122.45 mmol), and then the synthesis was carried out in the same manner as in the synthesis method of Sub4-19 to obtain 31.50 g (69%) of the product.

Compounds belong to Sub 4 are as follows, but are not limited thereto, and FD-MS values of the compounds are shown in Table 6 below.

TABLE 6 Compound FD-MS Compound FD-MS Sub4-1 m/z = 112.01(C₆H₅Cl = 112.56) Sub4-2 m/z = 162.02(C₁₀H₇Cl = 162.62) Sub4-3 m/z = 188.04(C₁₂H₉Cl = 188.65) Sub4-4 m/z = 228.07(C₁₅H₁₃Cl = 228.72) Sub4-5 m/z = 352.1(C₂₅H₁₇Cl = 352.86) Sub4-6 m/z = 202.02(C₁₂H₇ClO = 202.64) Sub4-7 m/z = 344.04(C₂₂H₁₃ClS = 344.86) Sub4-8 m/z = 352.1(C₂₅H₁₇Cl = 352.86) Sub4-9 m/z = 168.07(C₁₀H₁₃Cl = 168.66) Sub4-10 m/z = 328.07(C₂₂H₁₃ClO = 328.8) Sub4-11 m/z = 262.05(C_(1s)H₁₁Cl = 262.74) Sub4-12 m/z = 113(C₅H₄ClN = 113.54) Sub4-13 m/z = 290.06(C_(l8)H₁₁ClN₂ = 290.75) Sub4-14 m/2 = 266.06(C₁₆H₁₁ClN₂ = 266.73) Sub4-15 m/z = 317.07(C₁₉H₁₂ClN₃ = 317.78) Sub4-16 m/z = 266.06(C₁₆H₁₁ClN₂ = 266.73) Sub4-17 m/z = 240.05(C₁₄H₉ClN₂ = 240.69) Sub4-18 m/z = 316.08(C₂₀H₁₃ClN₂ = 316.79) Sub4-19 m/z = 267.06(C₁₅H₁₀ClN₃ = 267.72) Sub4-20 m/z = 240.05(C₁₄H₉ClN₂ = 240.69) Sub4-21 m/z = 342.09(C₂₂H₁₅ClN₂ = 342.83) Sub4-22 m/z = 296.02(C₁₆H₉ClN₂S = 296.77) Sub4-23 m/z = 245.08(C₁₄H₄D₅ClN₂ = 245.72) Sub4-24 m/z = 304.08(C₁₉H₁₃ClN₂ = 304.78) Sub4-25 m/z = 266.06(C₁₆H₁₁ClN₂ = 266.73) Sub4-26 m/z = 370.09(C₂₃H₁₅ClN₂O = 370.84) Sub4-27 m/z = 406.09(C₂₆H₁₅ClN₂O = 406.87) Sub4-28 m/z = 188.04(C₁₂H₉Cl = 188.65) Sub4-29 m/z = 267.06(C₁₅H₁₀ClN₃ = 267.72) Sub4-30 m/z = 290.09(C₂₀H₁₅Cl = 290.79) Sub4-31 m/z = 162(C₈H₃ClN₂ = 162.58) Sub4-32 m/z = 214.03(C₁₂H₇ClN₂ = 214.65) Sub4-33 m/z = 214.03(C₁₂H₇ClN₂ = 214.65) Sub4-34 m/z = 422.06(C₂₆H₁₅ClN₂S = 422.93) Sub4-35 m/z = 214.03(C₁₂H₇ClN₂ = 214.65) Sub4-36 m/z = 422.06(C₂₆H₁₅ClN₂S = 422.93) Sub4-37 m/z = 164.01(C_(s)H₅ClN₂ = 164.59) Sub4-38 m/z = 316.08(C₂₀H₁₃ClN₂ = 316.79) Sub4-39 m/z = 113(C₅H₄ClN = 113.54) Sub4-40 m/z = 118.05(C₆H_(l1)Cl = 118.6) Sub4-41 m/z = 19O.O3(C₁₀H₇ClN₂ = 190.63) Sub4-42 m/z = 114(C₄H₃ClN₂ = 114.53) Sub4-43 m/z = 19O.O3(C₁₀H₇ClN₂ = 190.63) Sub4-44 m/z = 521.13(C₃₄H₂₀ClN₃O = 522) Sub4-45 m/z = 537.13(C₃₆H₂₄ClNS = 538.11) Sub4-46 m/z = 404.11(C₂₇H₁₇ClN₂ = 404.9) Sub4-47 m/z = 372.05(C₂₂H₁₃ClN₂S = 372.87) Sub4-48 m/z = 280.04(C₁₆H₉ClN₂O = 280.71) Sub4-49 m/z = 396.05(C₂₄H₁₃ClN₂S = 396.89) Sub4-50 m/z = 311.02(C₁₇H₁₀ClNOS = 311.78) Sub4-51 m/z = 282.07(C₁₅H₁₁ClN₄ = 282.73) Sub4-52 m/z = 312.05(C₁₈H₁₄ClOP = 312.73) Sub4-53 m/z = 380.07(C₂₄H₁₃ClN₂O = 380.83) Sub4-54 m/z = 448.08(C₂₈H₁₇ClN₂S = 448.97) Sub4-55 m/z = 256.08(C₁₅H₁₃ClN₂ = 256.73) Sub4-56 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.9) Sub4-57 m/z = 367.09(C₂₃H₁₄ClN₃ = 367.84) Sub4-58 m/z = 367.11(C₂₅H₁₈ClN = 367.88) Sub4-59 m/z = 19O.O3(C₁₀H₇ClN₂ = 190.63) Sub4-60 m/z = 290.06(C₁₈H₁₁ClN₂ = 290.75) Sub4-61 m/z = 264.07(C₁₈H₁₃Cl = 264.75) Sub4-62 m/z = 572.17(C₃₉H₂₅ClN₂O = 573.09) Sub4-63 m/z = 523.15(C₃₄H₂₂ClN₃O = 5 24.02) Sub4-64 m/z = 278.05(C₁₈H₁₁ClO = 278.74) Sub4-65 m/z = 419.12(C₂₇H₁₈ClN₃ = 419.91) Sub4-66 m/z = 407.08(C₂₅H₁₄ClN₃O = 407.86) Sub4-67 m/z = 5 11.08(C₃₃H₁₈ClNOS = 512.02) Sub4-68 m/z = 240.05(C₁₄H₉ClN₂ = 240.69) Sub4-69 m/z = 572.14(C₃₇H₂₁ClN₄O = 573.05) Sub4-70 m/z = 407.08(C₂₅H₁₄ClN₃O = 407.86) Sub4-71 m/z = 342.09(C₂₂H₁₅ClN₂ = 342.83) Sub4-72 m/z = 362.12(C₂₂H₁₉ClN₂O = 362.86) Sub4-73 m/z = 340.08(C₂₂H₁₄ClN₂ = 340.81) Sub4-74 m/z = 277.07(C₁₈H₁₂ClN = 277.75) Sub4-75 m/z = 350.09(C₂₅H₁₅Cl = 350.85) Sub4-76 m/z = 354.09(C₂₃H₁₅ClN₂ = 354.84) Sub4-77 m/z = 267.06(C₁₅H₁₀ClN₃ = 267.72) Sub4-78 m/z = 267.06(C₁₅H₁₀ClN₃ = 267.72) Sub4-79 m/z = 470.13(C₃₀H₁₉ClN₄ = 470.96) Sub4-80 m/z = 359.08(C21H14ClN3O = 359.81) Sub4-81 m/z = 460.08(C₂₉H₁₇ClN₂S = 460.98) Sub4-82 m/z = 240.05(C14H9ClN2 = 240.69) Sub4-83 m/z = 510.08(C34H19ClOS = 511.04) Sub4-84 m/z = 444.1(C29H17ClN2O = 444.92) Sub4-85 m/z = 443.12(C₂₉H₁₈ClN₃ = 443.93) Sub4-86 m/z = 529.14(C₃₃H₂₄ClN₃S = 530.09) Sub4-87 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.9) Sub4 88 m/z = 357.07(C₂₁H₁₂ClN₃O = 357.8) Sub4-89 m/z = 357.07(C₂₁H₁₂ClN₃O = 357.8) Sub4-90 m/z = 449.08(C₂₇H₁₆ClN₃S = 449.96) Sub4-91 m/z = 373.04(C₂₁H₁₂ClN₃S = 373.86) Sub4-92 m/z = 423.06(C₂₅H₁₄ClN₃S = 423.92) Sub4-93 m/z = 458.09(C_(2S)H₁₅ClN₄O = 458.91) Sub4-94 m/z = 449.08(C₂₇H₁₆ClN₃S = 449.96) Sub4-95 m/z = 555.15(C₃₅H₂₆ClN₃S = 556.12) Sub4-96 m/z = 449.08(C₂₇H₁₆ClN₃S = 449.96) Sub4-97 m/z = 549.11(C₃₅H₂₀ClN₃S = 550.08) Sub4-98 m/z = 533.13(C₃₅H₂₀ClN₃O = 534.02) Sub4-99 m/z = 615.13(C₃₉H₂₂ClN₃O₃ = 616.07) Sub4-100 m/z = 357.07(C₂₁H_(I2)ClN₃O = 357.8) Sub4-101 m/z = 635.18(C₄₃H₂₆ClN₃O = 636.15) Sub4-102 m/2 = 289.07(C₁₉H₁₂ClN = 289.76) Sub4-103 m/z = 438.13(C₂₇H₁₁D₅ClN₃O = 438.93) Sub4-104 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.9) Sub4-105 m/z = 372.05(C₂₂H₁₁ClN₂S = 372.87) Sub4-106 m/z = 279.06(C₁₆H₁₀ClN₃ = 279.73)

Synthesis Example of Final Product 1. Synthesis of Z1-15

Sub 3-1 (16 g, 34.91 mmol) and Sub 4-15 (13.31 g, 41.889 mmol) were placed in a round-bottom flask and the mixture was dissolved in THF (128 ml). Pd(PPh₃)₄ (1.61 g, 1.40 mmol), K₂CO₃ (14.47 g, 104.72 mmol) and water (64 ml) were placed into the round-bottom flask and the mixture was stirred under reflux. When the reaction was completed, the reaction product was extracted with ether and water and an organic layer was concentrated. The concentrated organic layer was dried over MgSO₄ and concentrated once more. The final concentrate was separated by a silica gel column and recrystallized to obtain 17.14 g (yield 80%) of a product.

2. Synthesis of Z1-35

Sub 3-14 (12 g, 23.60 mmol and Sub 4-38 (8.97 g, 28.32 mmol) were placed in a round-bottom flask and the mixture was dissolved in THF. Pd(PPh₃)₄ (0.04 eq.), K₂CO₃ (3 eq.) and water were added into the round-bottom flask, and then the synthesis was carried out in the same manner as in the synthesis method of Z1-15 to obtain 11.26 g (yield 72%) of the product.

3. Synthesis of Z2-1

Sub 3-19 (21 g, 44.26 mmol) and Sub 4-48 (14.91 g, 53.12 mmol) were placed in a round-bottom flask and the mixture was dissolved in THF. Pd(PPh₃)₄ (0.04 eq.), K₂CO₃ (3 eq.) and water were added into the round-bottom flask, and then the synthesis was carried out in the same manner as in the synthesis method of Z1-15 to obtain 20.20 g (yield 77%) of the product.

4. Synthesis of Z3-12

Sub 3-38 (19 g, 35.62 mmol) and Sub 4-79 (20.13 g, 42.74 mmol) were placed in a round-bottom flask and the mixture was dissolved in THF. Pd(PPh₃)₄ (0.04 eq.), K₂CO₃ (3 eq.) and water were added into the round-bottom flask, and then the synthesis was carried out in the same manner as in the synthesis method of Z1-15 to obtain 22.49 g (yield 75%) of the product.

5. Synthesis of Z3-33

After Sub3-42 (15 g, 29.56 mmol) was dissolved in toluene (296 mL), Sub4-98 (15.79 g, 29.56 mmol), Pd₂(dba)₃ (0.81 g, 0.89 mmol), P(t-Bu)₃ (0.48 g, 2.36 mmol) and NaOt-Bu (8.52 g, 88.68 mmol) were added to the solution and the mixture was stirred at 60° C. When the reaction was completed, the reaction product was extracted with CH₂Cl₂ and water and an organic layer was dried over MgSO₄ and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 18.19 g (yield 70%) of a product.

6. Synthesis of Z3-43

Sub 3-49 (8 g, 14.61 mmol) and Sub 4-106 (4.91 g, 17.54 mmol) were placed in a round-bottom flask and the mixture was dissolved in anhydrous THF. Pd(PPh₃)₄ (0.04 eq.), K₂CO₃ (3 eq.), anhydrous THF and water were added into the round-bottom flask, and then the synthesis was carried out in the same manner as in the synthesis method of Z1-15 to obtain 6.61 g (yield 68%) of the product.

FD-MS values of the compounds Z1-1 to Z3-43 of the present invention synthesized by the above synthesis method are shown in Table 7 below.

Tab1e 7 Compound FD-MS Compound FD-MS Z1-1  m/z = 408.15(C₃₁H₂₀O = 408.5) Z1-2  m/z = 458.17(C₃₅H₂₂O = 458.56) Z1-3  m/z = 484.18(C₃₇H₂₄O = 484.6) Z1-4  m/z = 524.21(C₄₀H₂₈O = 524.66) Z1-5  m/z = 648.25(C₅₀H₃₂O = 648.81) Z1-6  m/z = 498.16(C₃₇H₂₂O₂ = 498.58) Z1-7  m/z = 640.19(C₄₇H₂₈OS = 640.8) Z1-8  m/z = 648.25(C₅₀H₃₂O = 648.81) Z1-9  m/z = 464.21(C₃₅H₂₈O = 464.61) Z1-10 m/z = 624.21(C₄₇H₂₈O₂ = 624.74) Z1-11 m/z = 558.2(C₄₃H₂₆O = 558.68) Z1-12 m/z = 409.15(C₃₀H₁₉NO = 409.49) Z1-13 m/z = 586.2(C₄₃H₂₆N₂O = 586.69) Z1-14 m/z = 562.2(C₄₁H₂₆N₂O = 562.67) Z1-15 m/z = 613.22(C₄₄H₂₇N₃O = 613.72) Z1-16 m/z = 562.2(C₄₁H₂₆N₂O = 562.67) Z1-17 m/z = 536.19(C₃₉H₂₄N₂O = 536.63) Z1-18 m/z = 612.22(C₄₅H₂₈N₂O = 612.73) Z1-19 m/z = 563.2(C₄₀H₂₅N₃O = 563.66) Z1-20 m/z = 536.19(C₃₉H₂₄N₂O = 536 63) Z1-21 m/z = 638.24(C₄₇H₃₀N₂O = 638.77) Z1-22 m/z = 592.16(C₄₁H₂₄N₂OS = 592.72) Z1-23 m/z = 541.22(C₃₉H₁₉D₅N₂O = 541.66) Z1-24 m/z = 600.22(C₄₄H₂₈N₂O = 600.72) Z1-25 m/z = 562.2(C₄₁H₂₆N₂O = 562.67) Z1-26 m/z = 666.23(C₄₈H₃₀N₂O₂ = 666.78) Z1-27 m/z = 702.23(C₅₁H₃₀N₂O₂ = 702.81) Z1-28 m/z = 688.25(C₅₁H₃₂N₂O = 688.83) Z1-29 m/z = 689.22(C₄₈H₂₇N₅O = 689.78) Z1-30 m/z = 764.28(C₅₇H₃₆N₂O = 764.93) Z1-31 m/z = 718.21(C₅₁H₃₀N₂OS = 718.87) Z1-32 m/z = 942.34(C₆₉H₄₂N₄O = 943.12) Z1-33 m/z = 642.18(C₄₅H₂₆N₂OS = 642.78) Z1-34 m/z = 510.17(C₃₇H₂₂N₂O = 510.6) Z1-35 m/z = 662.24(C₄₉H₃₀N₂O = 662.79) Z1-36 m/z = 539.19(C₃₉H₂₅NO₂ = 539.63) Z1-37 m/z = 668.28(C₄₉H₃₆N₂O = 668.84) Z1-38 m/z = 586.2(C₄₃H₂₆N₂O = 586.69) Z1-39 m/z = 817.27(C₅₉H₃₅N₃O₂ = 817.95) Z1-40 m/z = 833.28(C₆₁H₃₉NOS = 834.05) Z1-41 m/z = 562.2(C₄₁H₂₆N₂O = 562.67) Z2-1  m/z = 592.16(C₄₁H₂₄N₂OS = 592.72) Z2-2  m/z = 629.19(C₄₄H₂₇N₃S = 629.78) Z2-3  m/z = 716.23(C₅₂H₃₂N₂S = 716.9) Z2-4  m/z = 760.2(C₅₃H₃₂N₂S₂ = 760.97) Z2-5  m/z = 552.17(C₃₉H₂₄N₂S = 552.7) Z2-6  m/z = 708.17(C₄₉H₂₈N₂S₂ = 708.9) Z2-7  m/z = 641.13(C₄₂H₂₄FNOS₂ = 641.78) Z2-8  m/z = 594.19(C₄₀H₂₆N₄S = 594.74) Z2-9  m/z = 568.2(C₄₀H₂₈N₂S = 568.74) Z2-10 m/z = 760.2(C₅₃H₃₂N₂S₂ = 760.97) Z2-11 m/z = 692.19(C₄₉H₂₈N₂OS = 692.84) Z2-12 m/z = 555.18(C₃₈H₂₅N₃S = 555.7) Z2-13 m/z = 624.17(C₄₃H₂₉OPS = 624.74) Z2-14 m/z = 745.22(C₅₂H₃₁N₃OS = 745.9) Z2-15 m/z = 679.23(C₅₀H₃₃NS = 679.88) Z2-16 m/z = 652.2(C₄₇H₂₈N₂S = 652.82) Z2-17 m/z = 626.21(C₄₇H₃₀S = 626.82) Z2-18 m/z = 729.22(C₅₂H₃₁N₃S = 729.9) Z2-19 m/z = 633.23(C₄₅H₂₃D₅N₂S = 633.82) Z2-20 m/z = 728.23(C₅₃H₃₂N₂S = 728.91) Z2-21 m/z = 772.29(C₅₆H₄₀N₂S = 773.01) Z2-22 m/z = 961.31(C₅₉H₄₃N₃OS = 962.18) Z2-23 m/z = 884.26(C₆₂H₃₆N₄OS = 885.06) Z2-24 m/z = 835.27(C₅₉H₃₇N₃OS = 836.03) Z2-25 m/z = 719.2(C₅₀H₂₉N₃OS = 719.86) Z2-26 m/z = 719.2(C₅₀H₂₉N₃OS = 719.86) Z2-27 m/z = 719.2(C₅₀H₂₉N₃OS = 719.86) Z2-28 m/z = 823.2(C₅₈H₃₃NOS₂ = 824.03) Z2-29 m/z = 794.24(C₅₇H₃₄N₂OS = 794.97) Z2-30 m/z = 731.24(C₅₂H₃₃N₃S = 731.92) Z3-1  m/z = 713.28(C₅₃H₃₅N₃ = 713.88) Z3-2  m/z = 733.31(C₅₃H₃₉N₃O = 733.92) Z3-3  m/z = 711.27(C₅₃H₃₃N₃ = 711.87) Z3-4  m/z = 802.31(C₅₉H₃₈N₄ = 802.98) Z3-5  m/z = 725.28(C₅₄H₃₅N₃ = 725.9) Z3-6  m/z = 721.28(C₅₆H₃₅N = 721.9) Z3-7  m/z = 648.26(C₄₉H₃₂N₂ = 648.81) Z3-8  m/z = 726.3(C₅₅H₃₈N₂ = 726.92) Z3-9  m/z = 638.25(C₄₆H₃₀N₄ = 638.77) Z3-10 m/z = 638.25(C₄₆H₃₀N₄ = 638.77) Z3-11 m/z = 688.26(C₅₀H₃₂N₄ = 688.83) Z3-12 m/z = 841.32(C₆₁H₃₉N₅ = 842.02) Z3-13 m/z = 730.27(C₅₂H₃₄N₄O = 730.87) Z3-14 m/z = 831.27(C₆₀H₃₇N₃S = 832.04) Z3-15 m/z = 611.24(C₄₅H₂₉N₃ = 611.75) Z3-16 m/z = 883.27(C₆₃H₃₇N₃OS = 884.07) Z3-17 m/z = 865.31(C₆₄H₃₉N₃O = 866.04) Z3-18 m/z = 738.28(C₅₄H₃₄N₄ = 738.89) Z3-19 m/z = 788.29(C₅₈H₃₆N₄ = 788.95) Z3-20 m/z = 900.33(C₆₄H₄₄N₄S = 901.14) Z3-21 m/z = 652.23(C₄₆H₂₈N₄O = 652.76) Z3-22 m/z = 728.26(C₅₂H₃₂N₄O = 728.86) Z3-23 m/z = 728.26(C₅₂H₃₂N₄O = 728.86) Z3-24 m/z = 818.27(C₅₈H₃₄N₄O₂ = 818.94) Z3-25 m/z = 744.23(C₅₂H₃₂N₄S = 744.92) Z3-26 m/z = 724.27(C₅₀H₃₆N₄S = 724.93) Z3-27 m/z = 718.22(C₅₀H₃₀N₄S = 718.88) Z3-28 m/z = 753.25(C₅₃H₃₁N₅O = 753.87) Z3-29 m/z = 744.23(C₅₂H₃₂N₄S = 744.92) Z3-30 m/z = 850.31(C₆₀H₄₂N₄S = 851.08) Z3-31 m/z = 762.23(C₅₂H₃₁FN₄S = 762.91)  23-32 m/z = 844.27(C₆₀H₃₆N₄S = 845.04) Z3-33 m/z = 878.3(C₆₄H₃₈N₄O = 879.04) Z3-34 m/z = 910.29(C₆₄H₃₈N₄O₃ = 911.03) Z3-35 m/z = 930.34(C₆₈H₄₂N₄O = 931.11) Z3-36 m/z = 731.24(C₄₉H₂₉N₇O = 731.82) Z3-37 m/z = 733.29(C₅₂H₂₇D₅N₄O = 733.89) Z3-38 m/z = 728.26(C₅₂H₃₂N₄O = 728.86) Z3-39 m/z = 727.27(C₅₂H₃₃N₅ = 727.87) Z3-40 m/z = 673.25(C₅₀H₃₁N₃ = 673.82) Z3-41 m/z = 773.2(C₅₃H₃₁N₃S₂ = 773.97) Z3-42 m/z = 663.27(C₄₉H₃₃N₃ = 663.82) Z3-43 m/z = 664.23(C₄₇H₂₈N₄O = 664.77)

Manufacturing and Evaluation of Organic Electric Element [Test Example 1] to [Test Example 20] Red Organic Electroluminescent Element (Mixed-Phosphorescent Host of a Light Emitting Layer)

After A hole injection layer having a thickness of 60 nm was formed by vacuum-deposition of 4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter, abbreviated as 2-TNATA) on an ITO layer (anode), N,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine (hereinafter, abbreviated as NPB) was vacuum-deposited to a thickness of 60 nm to form a hole transport layer on the hole injection layer.

Next, as shown in Table 8 below, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer, wherein a mixture of compound represented by Formula 1 (first host) and compound represented by Formula 2 (second host) in a ratio of 3:7 was used as host, and bis-(1-phenylisoquinolyl)iridium (III)acetylacetonate (hereinafter, abbreviated as (piq)₂Ir(acac)) was used as dopant, and the dopant was doped so that the host and dopant had a weight ratio of 95:5.

Thereafter, (1,1′-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter, abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light-emitting layer to form a hole blocking layer and tris-(8-hydroxyquinoline)aluminum (hereinafter, abbreviated as “Alq₃”) was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.

Thereafter, LiF was deposited to a thickness of 0.2 nm to form, and then Al was deposited to a thickness of 150 nm to form a cathode.

[Comparative Example 1] to [Comparative Example 4]

Organic electroluminescent element was manufactured in the same manner as in Test Example 1, except that Compound 11-4, 12-1, Z1-42 or Z1-43 was each used alone as host of the light emitting layer.

[Comparative Example 5] and [Comparative Example 6]

Organic electroluminescent element was manufactured in the same manner as in Test Example 1, except that the following comparative compound 1 was used as the first host material of the light emitting layer, and the compound Z1-42 or Z1-43 was used as the second host material.

[Comparative Example 7] and [Comparative Example 8]

Organic electroluminescent element was manufactured in the same manner as in Test Example 1, except that the following comparative compound 2 was used as the first host material of the light emitting layer, and the compound Z1-42 or Z1-43 was used as the second host material.

A forward bias DC voltage was applied to the o electroluminescent elements manufactured in Test Examples 1 to 65 and Comparative Examples 1 to 8 and electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photo research and lifetime (T95) was measured with a lifetime measuring device manufactured by Mc Science at 2500 cd/m² standard luminance. The measurement results are shown in Table 8 below.

TABLE 8 Current Voltage Density Brightness Efficiency Lifetime Host 1 Host 2 (V) (mA/cm²) (cd/m²) (cd/A) T(95) comp. Ex(1) 11-4 — 6.1 16.4 2500 15.2 82.4 comp. Ex(2) 12-1 — 5.8 13.5 2500 18.5 93.7 comp. Ex(3)  Z1-42 5.6 12.6 2500 19.9 100.1 comp. Ex(4)  Z1-43 5.6 13.0 2500 19.3 101.4 comp. Ex(5) Comp. compd1 Z1-42 5.4 8.8 2500 28.4 112.7 comp. Ex(6) Z1-43 5.4 9.0 2500 27.8 113.4 comp. Ex(7) Comp. compd2 Z1-42 5.5 9.2 2500 27.3 111.9 comp. Ex(8) Z1-43 5.5 9.4 2500 26.7 112.2 Test Ex. (1)  3-32 Z1-15 4.9 6.4 2500 39.2 137.2 Test Ex. (2) Z1-23 4.9 6.3 2500 39.4 137.5 Test Ex. (3) Z1-27 5.0 6.4 2500 39.0 136.7 Test Ex. (4) Z1-33 5.0 6.5 2500 38.3 136.5 Test Ex. (5) Z1-42 5.1 6.6 2500 37.7 135.9 Test Ex. (6) Z1-43 5.1 6.7 2500 37.5 135.6 Test Ex. (7) Z2-13 5.1 6.7 2500 37.3 135.2 Test Ex. (8) Z2-21 5.1 6.7 2500 37.1 134.8 Test Ex. (9) Z2-30 4.9 6.5 2500 38.5 136.8 Test Ex. (10) Z3-1  4.9 6.4 2500 38.8 137.0 Test Ex. (11) Z3-10 4.9 6.4 2500 39.3 137.4 Test Ex. (12) Z3-32 5.0 6.6 2500 38.1 136.3 Test Ex. (13) Z3-41 5.0 6.6 2500 37.9 136.1 Test Ex. (14)  4-21 Z1-15 4.8 6.6 2500 37.7 135.2 Test Ex. (15) Z1-23 4.8 6.6 2500 38.0 135.6 Test Ex. (16) Z1-27 4.9 6.7 2500 37.5 134.5 Test Ex. (17) Z1-33 4.9 6.8 2500 37.0 134.2 Test Ex. (18) Z1-42 5.0 6.8 2500 36.5 133.5 Test Ex. (19) Z1-43 5.0 6.9 2500 36.2 133.3 Test Ex. (20) Z2-13 5.0 6.9 2500 36.0 133.0 Test Ex. (21) Z2-21 5.0 7.0 2500 35.6 132.8 Test Ex. (22) Z2-30 4.8 6.7 2500 37.1 134.7 Test Ex. (23) Z3-1  4.8 6.7 2500 37.3 135.0 Test Ex. (24) Z3-10 4.8 6.6 2500 37.8 135.3 Test Ex. (25) Z3-32 4.9 6.8 2500 36.9 134.1 Test Ex. (26) Z3-41 4.9 6.8 2500 36.7 133.8 Test Ex. (27)  10-41 Z1-15 4.7 6.0 2500 41.8 141.1 Test Ex. (28) Z1-23 4.7 5.9 2500 42.4 141.5 Test Ex. (29) Z1-27 4.8 6.0 2500 41.5 140.1 Test Ex. (30) Z1-33 4.8 6.1 2500 40.9 139.7 Test Ex. (31) Z1-42 4.9 6.2 2500 40.2 139.1 Test Ex. (32) Z1-43 4.9 6.3 2500 40.0 138.9 Test Ex. (33) Z2-13 4.9 6.3 2500 39.7 138.8 Test Ex. (34) Z2-21 4.9 6.3 2500 39.5 138.6 Test Ex. (35) Z2-30 4.7 6.1 2500 41.1 140.3 Test Ex. (36) Z3-1  4.7 6.1 2500 41.3 140.8 Test Ex. (37) Z3-10 4.7 5.9 2500 42.1 141.3 Test Ex. (38) Z3-32 4.8 6.2 2500 40.6 139.5 Test Ex. (39) Z3-41 4.8 6.2 2500 40.3 139.3 Test Ex. (40) 11-4 Z1-15 5.0 6.9 2500 36.1 133.3 Test Ex. (41) Z1-23 5.0 6.8 2500 36.5 133.6 Test Ex. (42) Z1-27 5.1 7.0 2500 35.9 132.8 Test Ex. (43) Z1-33 5.1 7.1 2500 35.4 132.6 Test Ex. (44) Z1-42 5.2 7.2 2500 34.9 131.8 Test Ex. (45) Z1-43 5.2 7.2 2500 34.7 131.5 Test Ex. (46) Z2-13 5.2 7.3 2500 34.4 131.2 Test Ex. (47) Z2-21 5.2 7.3 2500 34.1 130.8 Test Ex. (48) Z2-30 5.0 7.0 2500 35.5 132.9 Test Ex. (49) Z3-1  5.0 7.0 2500 35.8 133.1 Test Ex. (50) Z3-10 5.0 6.9 2500 36.3 133.4 Test Ex. (51) Z3-32 5.1 7.1 2500 35.2 132.4 Test Ex. (52) Z3-41 5.1 7.1 2500 35.0 132.2 Test Ex. (53) 12-1 Z1-15 4.6 6.2 2500 40.2 139.1 Test Ex. (54) Z1-23 4.6 6.2 2500 40.5 139.6 Test Ex. (55) Z1-27 4.7 6.3 2500 40.0 138.5 Test Ex. (56) Z1-33 4.7 6.3 2500 39.6 138.3 Test Ex. (57) Z1-42 4.8 6.4 2500 39.0 137.5 Test Ex. (58) Z1-43 4.8 6.4 2500 38.8 137.3 Test Ex. (59) Z2-13 4.8 6.5 2500 38.6 137.0 Test Ex. (60) Z2-21 4.8 6.5 2500 38.5 136.7 Test Ex. (61) Z2-30 4.6 6.3 2500 39.7 138.6 Test Ex. (62) Z3-1  4.6 6.3 2500 39.9 138.9 Test Ex. (63) Z3-10 4.6 6.2 2500 40.4 139.4 Test Ex. (64) Z3-32 4.7 6.4 2500 39.3 138.1 Test Ex. (65) Z3-41 4.7 6.4 2500 39.1 137.7

As can be seen from Table 8, in Comparative Examples 5-8, the characteristics of element were improved compared to Comparative Examples 1-4, and the element characteristics of the present invention were the best, wherein a single material included in Formula 1 or Formula 2 was used as host in Comparative Examples 1-4, a mixture of material included in Formula 2 of the present invention and comparative compound was used as host in Comparative Examples 5-8, and a mixture of compound included in Formula 1 and compound included in Formula 2 was used as host in the present invention.

The reason why the element characteristics of the embodiment of the present invention are the best is as follows. When the compound represented by Formula 1, which has minimal differences in HOMO energy level from the hole transport material, is used as a host, a hole transport from the hole transport layer to a light emitting layer is facilitated, so that holes can be provided to the light emitting layer more quickly. In addition, since the compound represented by Formula 2 of the present invention having a condensed structure has a deep (low) LUMO energy level, the difference of LUMO energy level between the electron transport material is minimized to facilitate the movement of electrons. As a result, the efficiency is improved and the thermal stability is also improved due to the high Tg value.

That is, when the compound represented by Formula 1 and the compound represented by Formula 2 of the present invention are mixed, the injection/transport capability of holes and electrons toward the light emitting layer is improved and the stability is increased. As a result, it seems that the overall driving of the element is improved, the efficiency is increased because the charge balance in the light emitting layer of holes and electrons is increased, so that light emission occurs well inside the light emitting layer rather than the hole transport layer interface, and the overall lifespan of the element is maximized because the deterioration of the HTL interface is also reduced.

This suggests that the entire performance of the element can be improved by electrochemically synergistic action when the compound represented by Formula 1 and the compound represented by Formula 2 are combined and used as a host.

[Test Example 66] and [Test Example 67]

Organic electroluminescent element was manufactured in the same manner as in Test Example 41, except for changing the mixing ratio of the first host and the second host as shown in Table 9 below.

[Test Example 68] and [Test Example 69]

Organic electroluminescent element was manufactured in the same manner as in Test Example 54, except for changing the mixing ratio of the first host and the second host as shown in Table 9 below.

TABLE 9 mixing ratio Current (Host 1: Voltage Density Brightness Efficiency Lifetime Host 1 Host 2 Host 2) (V) (mA/cm²) (cd/m²) (cd/A) T(95) Test Ex. (41) 3:7 5.0 6.8 2500 36.5 133.6 Test Ex. (66) 11-4 Z1-23 5:5 5.1 7.1 2500 35.1 132.4 Test Ex. (67) 7:3 5.1 7.5 2500 33.4 131.7 Test Ex. (54) 3:7 4.6 6.2 2500 40.5 139.6 Test Ex. (68) 12-1 Z1-23 5:5 4.8 6.3 2500 39.8 138.0 Test Ex. (69) 7:3 4.9 6.4 2500 39.1 137.2

As can be seen from Table 9 above, when the mixing ratio of the first host and the second host is changed, the driving voltage, lifespan and efficiency are slightly different. When the first host and the second host are mixed in a ratio of 3:7, the driving voltage, efficiency and lifespan were the best, and as the mixing ratio of the first host was increased, the efficiency and lifespan were slightly decreased.

This result shows that the mixing ratio of a mixture affects the characteristics of the element, and it is suggested that each component of the mixture needs to be properly mixed so that the charge balance in the light emitting layer can be maximized.

Although the exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art to which the present invention pertains will be capable of various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiment disclosed herein is intended to illustrate the present invention rather than to limit the present invention and the scope of the present invention is not limited by the embodiments. The scope of the present invention shall be construed on the basis of the accompanying claims, and it shall be construed that all of the technical ideas included within the scope equivalent to the claims belong to the present invention. 

1: An organic electric element comprising: a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode, the organic material layer comprising a phosphorescent light emitting layer including a host, the host comprising a first compound represented by the following Formula 1 and a second compound represented by the following Formula 2:

wherein: Ar₁ to Ar₃, Ar₅, Ar₆ and Ar¹ are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and -L′-N(R_(a))(R_(b)), L₁ to L₆, L¹ are each independently selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₃-C₆₀ aliphatic ring, and a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, X¹ is N-L^(a)-Ar^(a), O or S, R¹ to R⁴ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a C₁-C₃₀ alkyl group, a C₂-C₃₀ alkenyl group, a C₂-C₃₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)), and neighboring groups may be bonded to each other to form a ring, n is 0 or 1, m is 1 or 2, and when m is 2, each of a plurality of L₂s, each of a plurality of L₃s, each of a plurality of Ar₂s, and each of a plurality of Ar₃s are the same as or different from each other, l is an integer of 0 to 4, and 1 is not 0 when X¹ is O or S, when l is an integer of 2 or more, each of a plurality of L¹s, each of a plurality of Ar¹s are the same as or different from each other, p, q, r and s are an integer of 0 to 4, and where each of these is an integer of 2 or more, each of R¹s, each of R²s, each of R³s and each of R⁴s are the same as or different from each other, L′ and L^(a) are each independently selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₃-C₆₀ aliphatic ring, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a combination thereof, R_(a), R_(b) and Ar^(a) are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₃-C₆₀ aliphatic ring, and a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and Ar₁ to Ar₃, Ar₅, Ar₆, Ar¹, L₁ to L₆, L¹, R¹ to R⁴, L′, L^(a), Ar^(a), R_(a), R_(b) and the ring formed by linking neighboring groups to each other may be each substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀ arylalkenyl group. 2: The organic electric element of claim 1, wherein Formula 1 is represented by one of the following Formula 1-A-1 to Formula 1-A-5:

wherein: L₁ to L₃, Ar₂, Ar₃ and m are the same as defined in claim 1, L′ is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring, Ar′ is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, R₁, R₂, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and neighboring groups may be linked to each other to form a ring, and R′ and R″ may be linked to each other to form a ring, and a and c are each an integer of 0-4, b is an integer of 0-3, and where each of these is an integer of 2 or more, each of R₁s and each of R₂s are the same as or different from each other. 3: The organic electric element of claim 1, wherein Formula 1 is represented by one of the following Formula 1-B-1 to Formula 1-B-4:

wherein: L₁ to L₆, Ar₂, Ar₃, Ar₅ and Ar₆ are the same as defined in claim 1, L′ is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring, Ar′ is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, R₁, R₂, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and neighboring groups may be linked to each other to form a ring, and R′ and R″ may be linked to each other to form a ring, and a and b are each an integer of 0-3, and where each of these is an integer of 2 or more, each of R₁s and each of R₂s are the same as or different from each other. 4: The organic electric element of claim 1, wherein Formula 1 is represented by one of the following Formula 1-C-1 to Formula 1-C-4:

wherein: L₁ to L₆, Ar₂, Ar₃, Ar₅ and Ar₆ are the same as defined in claim 1, L′ is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring, Ar′ is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and R₁, R₂, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and neighboring groups may be linked to each other to form a ring, and R′ and R″ may be linked to each other to form a ring, and a is an integer of 0-4, b is an integer of 0-2, and where each of these is an integer of 2 or more, each of R₁s and each of R₂s are the same as or different from each other. 5: The organic electric element of claim 1, wherein Formula 1 is represented by one of the following Formula 1-E-1 to Formula 1-E-5:

wherein: L₁ to L₆, Ar₂, Ar₃, Ar₅ and Ar₆ are the same as defined in claim 1, R₃ to R₅ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and neighboring groups may be linked to each other to form a ring, and c is an integer of 0-5, d is an integer of 0-4, e is an integer of 0-3, and when each of these is an integer of 2 or more, each of R₃s, each of R₄s and each of R₅s are the same as or different from each other. 6: The organic electric element of claim 1, wherein Formula 2 is represented by one of the following Formulas 2-A-1 to 2-A-3:

wherein R¹ to R⁴, L^(a), Ar^(a), L¹, Ar¹, p to s, l are the same as defined in claim
 1. 7: The organic electric element of claim 1, wherein Formula 2 is represented by Formula 2-B-1:

wherein: R¹, R³, R⁴, p, r and s are the same as defined in claim 1, V is N-L_(a)-Ar_(a), C(R′)(R″), O or S, R⁵, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and neighboring groups may be linked to each other to form a ring, and R′ and R″ may be linked to each other to form a ring, t is an integer of 0-7, and when t is an integer of 2 or more, each of R⁵ s is the same as or different from each other, L_(a) is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring, and Ar_(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group. 8: The organic electric element of claim 1, wherein the ring formed by linking neighboring R¹s to each other, neighboring R²s to each other, neighboring R³s to each other, or neighboring R⁴s to each other is a ring represented by one of the following Formulas F-1 to F-4:

wherein: the dotted line is the condensation site, U is N-L_(a)-Ar_(a), C(R′)(R″), O or S, R¹⁰ to R¹³, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and neighboring groups may be linked to each other to form a ring, and R′ and R″ may be linked to each other to form a ring, and a1 and a3 are each an integer of 0-4, a2 and a4 are each an integer of 0-6, and where each of these is an integer of 2 or more, each of R¹⁰s, each of R¹¹s, each of R¹²s and each of R¹³s are the same as or different from each other, L_(a) is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring, and Ar_(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group. 9: The organic electric element of claim 1, wherein R¹ to R⁴ are one of the following Formula S-1 or S-2:

wherein: Y is N-L_(a)-Ar_(a), C(R′)(R″), O or S, Q¹ to Q⁵ are each independently N or C(R′), L_(A), L_(B) and L_(a) are each independently from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring, Ar_(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, neighboring groups may be linked to each other to form a ring, and R′ and R″ may be linked to each other to form a ring, A ring and B ring are each selected from the following structures:

wherein: * indicates a condensed position, Vs are each N or C(R′), at least one of Vs is N, W¹ and W² are each independently a single bond, N-L_(a)-Ar_(a), C(R′)(R″), O or S, and R′, R″, L_(a) and Ar_(a) are the same as defined in the above. 10: The organic electric element of claim 1, wherein Formula 2 is represented by one of the following Formula 2-C-1 to Formula 2-C-5:

wherein: R¹ to R⁴, X¹, L¹, p to s are the same as defined in claim 1, Y is N-L_(a)-Ar_(a), C(R′)(R″), O or S, Vs are each independently N or C(R′), Re, R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₆-C₂₀ arylthio, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group, and neighboring R's may be linked to each other to form a ring, and R′ and R″ may be linked to each other to form a ring, L_(a) is independently selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring, and Ar_(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a C₃-C₂₀ aliphatic ring group. 11: The organic electric element of claim 1, wherein the compound represented by Formula 1 is one of the following compounds:

12: The organic electric element of claim 1, wherein the compound represented by Formula 2 is one of the following compounds:

13: The organic electric element of claim 1, wherein the weight ratio of the first compound to the second compound is 2:8 to 8:2. 14: The organic electric element of claim 1, further comprising a layer for improving luminous efficiency, wherein the layer for improving luminous efficiency is formed on one side of both sides of the first electrode or the second electrode and the one side is not facing the organic material layer. 15: The organic electric element of claim 1, wherein the organic material layer comprises two or more stacks, and the stacks each comprise a hole transport layer, a light-emitting layer and an electron transport layer formed sequentially on the first electrode. 16: The organic electric element of claim 15, wherein the organic material layer further comprises a charge generation layer formed between the two or more stacks. 17: The organic electric element of claim 1, wherein the organic material layer further comprises one or more hole transport band layers formed between the light-emitting layer and the anode, and the hole transport band layers comprise at least one of a hole transport layer and an emission auxiliary layer comprising the formula
 1. 18: An electronic device comprising: a display device comprising organic electric element of claim 1; and a control unit for driving the display device. 19: The electronic device of claim 18, wherein the organic electric element is an organic electroluminescent element, an organic solar cell, an organic photo conductor, an organic transistor, an element for monochromatic illumination or a quantum dot display. 